Benzenesulfonyl carboxamide compounds intermediate compounds and methods of preparation thereof and use of said compounds and intermediate compounds as herbicidal agents

ABSTRACT

There are provided novel benzenesulfonyl carboxamide compounds and novel intermediate benzenesulfonyl-2-imidazolin-5-one compounds, novel intermediates and methods for the preparation of said compounds, and a method for controlling a variety of annual and perennial plant species utilizing novel benzenesulfonyl carboxamide compounds and novel intermediate benzenesulfonyl 2-imidazolin-5-one compounds.

This is a divisional of application(s) Ser. No. 08/887,952, filed onJul. 6, 1993, now U.S. Pat. No. 5,338,883, which is a divisional ofapplication Ser. No. 07/856,262, filed on Mar. 23, 1992, now U.S. Pat.No. 5,252,539, issued Oct. 12, 1993, which is a divisional ofapplication Ser. No. 07/611,626, filed on Nov. 13, 1990, now U.S. Pat.No. 5,120,854, issued Jun. 9, 1992, which is a divisional of applicationSer. No. 07/417,400, filed Oct. 5, 1989, now U.S. Pat. No. 4,992,094,issued Feb. 12, 1991, which is a divisional of application Ser/ No.07/214,507, filed Jul. 7, 1988, now U.S. Pat. No. 4,883,914, issued Nov.28, 1989, which in turn, is a continuation-in-part of application Ser.No. 07/806,416, filed Aug. 17, 1987, abandoned.

SUMMARY OF THE INVENTION

The invention is directed to certain herbicidal intermediatebenzenesulfonyl 2-imidazolin-5-one compounds of formula (I) and certainherbicidal benzenesulfonyl carboxamide compounds of formula (II)##STR1## wherein A in both formula (I) and (II) is hydrogen;

straight or branched C₁ -C₄ alkyl, optionally substituted with one tothree halogens, C₁ -C₄ alkoxy, C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl,C₁ -C₄ alkylsulfonyl, carboalkoxy, phenyl, or oxo;

straight or branched C₁ -C₄ alkenyl, optionally substituted with one tothree halogens or phenyl;

C₁ -C₄ alkynyl, optionally substituted with one to three halogens;

and additionally in formula (II) A is amino, optionally substituted withstraight or branched C₁ -C₆ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₄ haloalkyl,straight or branched C₁ -C₆ alkenyl, C₃ -C₆ cycloalkenyl, phenyl,benzyl,(di)alkylamino, or C₁ -C₄ alkoxy;

C₁ -C₄ alkoxy; or

C₁ -C₄ alkylthio;

R₁ is C₁ -C₄ alkyl;

R₂ is C₁ -C₄ alkyl or C₃ -C₆ cycloalkyl; and when R₁ and R₂ are takentogether with the carbon to which they are attached, they may be C₃ -C₆cycloalkyl optionally substituted with methyl;

and when R₁ and R₂ are not the same, thus creating an asymmetric center,the optical isomers thereof;

Q is represented by formula (III) ##STR2## wherein R₃ -R₇ are eachhydrogen; halogen; nitro; cyano;

straight or branched C₁ -C₄ alkyl, optionally substituted with one ormore halogens or phenyl;

straight or branched C₁ -C₄ alkenyl, optionally substituted with one tothree halogens;

OR₈ where R₈ is hydrogen; C₁ -C₄ alkyl, optionally substituted withhalogen(s), C₁ -C₄ alkoxy, or phenyl; or C₁ -C₄ alkenyl optionallysubstituted with one to three halogens or phenyl;

phenyl, optionally substituted with one to three halogens, one to threeC₁ -C₄ alkyl, one to three C₁ -C₄ alkoxy or one to two nitro;

C₁ -C₄ alkylcarbonyl, optionally substituted with halogen (s);

C₁ -C₄ alkylthio, optionally substituted with halogen (s);

C₁ -C₄ alkylsulfinyl, optionally substituted with halogen(s);

C₁ -C₄ alkylsulfonyl, optionally substituted with halogen (s);

amino, optionally substituted by C₁ -C₄ alkyl;

CO₂ R₉ where R₉ is hydrogen, C₁ -C₄ alkyl, optionally ally substitutedwith one to three halogens;

R₃ -R₄, R₄ -R₅, R₅ -R₆, R₆ -R₇ may also be --(CH═CH--CH═CH)-- which mayalso be optionally substituted with up to three of the substituentsdescribed for R₃ -R₇ above;

with the proviso that no more than three of R₃ -R₇ can be: cyano, nitro,(substituted)phenyl, alkylcarbonyl, alkylthio, alkylsulfinyl,alkylsulfonyl, amine, CO₂ R₉ ;

W is O or S;

Y is hydrogen; or a salt thereof, wherein Y is a cation.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

A preferred group of benzenesulfonyl carboxamides andbenzenesulfonyl-2-imidazolin-5-one compounds of formula II and formula Iabove are those wherein

A is hydrogen or methyl;

R₁ is methyl;

R₂ is isopropyl;

R₃ -R₇ are each halogen(s) and/or C₁ -C₄ alkyl, optionally substitutedwith halogen;

Y is hydrogen, or a cation of alkali metals, alkaline earth metals,manganese, copper, iron,

zinc, cobalt, lead, silver, nickel, ammonium and organic ammonium.

In formula (II) above, alkali metals include: sodium, potassium andlithium, but sodium is generally preferred. Further, the term "organicammonium" is defined as a group consisting of a positively chargednitrogen atom joined to from one to four groups, each containing fromone to 20 carbon atoms. Among the organic ammonium groups which areillustrative for the preparation of the organic ammonium salts of theformula (II) phenylsulfonyl carboxamide herein are: monoalkylammonium,dialkylammonium, trialkylammonium, tetraalkylammonium,monoalkenylammonium, dialkenylammonium, trialkenylammonium,monoalkynylammonium, dialkynylammonium, trialkynylammonium,monoalkanolammonium, dialkanolammonium, trialkanolammonium, C₃ -C₆cycloalkylammonium, piperidinium, morpholinium, pyrrolidinium,benzylammonium and equivalents thereof. Exemplary of halogen hereinaboveare chlorine, fluorine, bromine, and iodine, but chlorine, bromine andfluorine are preferred.

A more preferred group of formula (I) and formula (II) compounds arethose wherein

A is methyl;

R₁ is methyl;

R₂ is isopropyl;

R₃ is hydrogen, halogen or methyl;

R₅ is halogen or methyl, and

W is oxygen.

As indicated above, the present invention relates to novel formula (II)herbicidal benzenesulfonyl carboxamide compounds and novel formula (I)benzenesulfonyl-2-imidazolin-5-one compounds which can serve asintermediates for the preparation of said formula (II) compounds and,additionally, are themselves herbicidal. Thus benzenesulfonylcarboxamide compounds of formula (II) are readily prepared by treatmentof compounds of formula (I) with water optionally in the presence ofcatalytic amounts of an acid, in an inert solvent as illustrated in flowdiagram I below. ##STR3## wherein A, R₁, R₂ and Q are as describedabove, W is oxygen and Y is hydrogen.

Compounds of formula I for use in the above reaction may conveniently beprepared by the reaction of an α-aminoamide of formula (IV) with acarboxylic acid anhydride of formula (V) (or acid chloride or equivalentthereof), in an inert solvent, optionally in the presence of an acidacceptor to yield a formula (VI) 2-acetamido-2,3-disubstituted amidewhich may be cyclized by treatment with aqueous alkali to yieldimidazolinones of formula (VII). Alternatively imidazolinones of formula(VII) may be prepared directly by the reaction of a formula (IV)e-aminoamide with an ortho ester of formula VIII at elevated temperaturein an inert solvent. Imidazolinones of formula (I) may then be obtainedby treatment of the thus obtained formula (VIII) imidazolinone with abenzenesulfonyl chloride of formula (IX) in an inert solvent in thepresence of an acid acceptor such as triethylamine, pyridine, sodiumhydride or the like, and isolation of the desired formula (I) product bycareful exclusion of water in the workup. These reactions areillustrated in flow diagram (II) below. ##STR4## wherein A is hydrogen;C₁ -C₄ alkyl; C₁ -C₄ alkenyl; or C₁ -C₄ alkynyl each of which may beoptionally substituted as described above for formula (I) and (II), andR₁, R₂ and Q are as described for formula (I) and (II) above.

Compounds of formula (II) may also be prepared by hydrolysis ofcompounds of formula II where A is hydrogen with aqueous acid, forexample aqueous HCl, which may be isolated as2-amino-2,3-dialkyl-N-(benzenesulfonyl)carboxamide acid salts (i.e.hydrochlorides) of formula (X) or as their corresponding free baseswhich exist as zwitterions of formula (XI). The resulting formula (X) orformula (XI) compound upon reaction with a carboxylic acid anhydride offormula (V) or carboxylic acid chloride (or equivalent thereof) orisocyanate of formula XII in an inert solvent (optionally in thepresence of an acid acceptor) also yields compounds of formula (II) asillustrated in flow diagram (III) below. ##STR5## wherein B is(substituted) imino, substituted with straight or branched C₁ -C₆ alkyl,C₃ -C₆ cycloalkyl, C₁ -C₄ haloalkyl, straight or branched C₁ -C₆alkenyl, C₃ -C₆ cycloalkenyl, or phenyl, benzyl, (di)alkylamino or C₁-C₄ alkoxy.

Another method for the preparation of formula (II) benzenesulfonylcarboxamide compounds of the invention involves the sequential reactionof a formula (VI) 2-acetamido-2,3-disubstituted amide with sodiumhydride followed by reaction with a formula (IX) benzenesulfonylchloride in an inert solvent in a temperature range of about 20° C. toreflux as illustrated in flow diagram (IV) below. ##STR6## wherein A,R₁, R₂ and Q are as described for formula (II above).

Formula (II) benzenesulfonyl carboxamides may also be obtained byreaction of an e-amino acid of formula (XIII) with a carboxylic acidanhydride of formula (V) followed by reaction of the thus-formed formula(XIV) N-acylamino acid with either a dehydrating agent (such as aformula (V) anhydride or dicyclohexylcarbodiimide) to give azlactoneXVb, or reaction with an acylating reagent such as an alkylchloroformateto give a mixed anhydride XVa; the "activated" N-acylamino acids (XVa orXVb) are then reacted with an alkali metal salt of a benzenesulfonamideof formula (XVI) to afford, on acidification, compounds of formula (II)as illustrated in flow diagram (V) below. ##STR7## wherein A, R₁, R₂ andQ are as described above for formula (II), and M is an alkali metal.

Another method for the preparation of formula (II) benzenesulfonylcarboxamides involves the reaction of hydantoin compounds of formula(XVII) with benzenesulfonyl chlorides of formula (IX) in the presence ofan acid acceptor such as triethylamine, pyridine, sodium hydride or thelike, in an inert organic solvent to yield sulfonyl hydantoins offormula (XVIII). Formula (II) benzenesulfonylcarboxamide compounds ofthe invention may then be obtained by reaction of formula (XVIII)hydantoins with nucleophiles of formula (XIX) as illustrated in flowdiagram VI below. ##STR8## wherein A is amino, alkoxy or alkylthio whichmay optionally be substituted as described for formula (II); and R₁, R₂,Q and Y are as described by formula (II) above.

Salts of the benzenesulfonyl carboxamide compounds of this invention mayreadily be prepared by reaction of a compound of formula (II) where Y ishydrogen with a base such as ammonia, an organic ammonium compound, analkali or alkaline earth metal hydride or the like in an inert organicsolvent as illustrated in flow diagram (VII) below. ##STR9## wherein A,R₁, R₂, Q, W and Y are as previously described for formula (II).

The present invention includes novel formula (VI)2-acetamido-2,3-disubstituted amide, formula (VII) imidazolinone,formula (X) 2-amino-2,3-dialkyl-N(benzenesulfonyl)carboxamide, formula(XI) zwitterion, formula (XVb) oxazolinone, formula (XVII) hydantoin andformula (XVIII) benzenesulfonyl hydantoin, compounds as described abovein the flow diagrams which are intermediates useful for the preparationof novel formula (I) and novel formula (II) herbicidal compounds.

The formula (I) benzenesulfonyl-2-imidazolinone and formula (II)benzenesulfonyl carboxamide compounds of the present invention areeffective herbicidal agents useful for the control of a wide variety ofannual and perennial monocotyledonous and dicotyledonous plants. Thesecompounds may be applied to the foliage thereof or to soil or watercontaining seeds or other propagating organs of said plants such astubers, rhizomes or stolons, at rates of from about 0.032 to 4.0 kg/ha,and preferably at rates from about 0.5 to 2.0 kg/ha.

Rates of application above the 4.0 kg/ha level may be used toeffectively kill undesirable plant species. However, rates ofapplication of toxicant in excess of the level necessary to kill theundesirable plants may be is costly and serve no useful function in theenvironment.

Among the plants which may be controlled with the compounds of thisinvention are: Helianthus annuus, Sesbania exaltata, Sinapis arvensis,Abutilon theophrasti, Brassica napus, Ambrosia artemisifolia, Xanthiumstrumarium, Matricaria inodora, Chenopodium album, Amaranthusretroflexus, Cirsium arvense, Datura stramonium, Ipomoea hederacea, Sidaspinosa, Portulaca oleracea, Stellaria media, Calystegia sepium, Solanumcarolinense, Gallium aparine, Cassia obtusifolia.

It has also been found that many of the formula (I) and formula (II)compounds of the invention are selective herbicides when applied to thefoliage of plants or to soil containing seeds of said plants atrelatively low rates of application, i.e., at from 0.032 to about 2.0 kgper hectare, depending on the compound used and crop treated.

In particular many of the formula (I) and formula (II) compounds of theinvention have been found suitable for the control of undesirablebroadleaf weeds in the presence of agronomically important crops such ascorn, wheat, barley, soybeans, peanuts and the like.

Formula (II) wherein Y is a salt-forming cation, which are watersoluble, can simply be dispersed in water and applied as a diluteaqueous spray to the foliage of plants or to soil containing propagatingorgans thereof. These salts also lend themselves to formulation asflowable concentrates. While those salts which are soluble in organicsolvents, for example organic ammonium salts may be formulated asemulsifiable concentrates, suspension concentrates and the like.

The formula (I) and formula (II) compounds can also be formulated aswettable powders, flowable concentrates, emulsifiable concentrates,granular formulations and the like.

Wettable powders can be prepared by grinding together about 20% to 45%by weight of a finely divided carrier such as kaolin, bentonite,diatomaceous earth, attapulgite, or the like, about 45% to 80% by weightof the active compound, about 2% to 5% by weight of a dispersing agentsuch as sodium lignosulfonate, and about 2% to 5% by weight of anonionic surfactant, such as octylphenoxy polyethoxy ethanol,nonylphenoxy polyethoxy ethanol or the like.

A typical flowable liquid can be prepared by admixing about 40% byweight of the active ingredient with about 2% by weight of a gellingagent such as bentonite, about 3% by weight of a dispersing agent suchas sodium lignosulfonate, about 1% by weight of polyethylene glycol andabout 54% by weight of water.

A typical emulsifiable concentrate can be prepared by dissolving about5% to 25% by weight of the active ingredient in about 65% to 90% byweight of N-methylpyrrolidone, isophorone, butyl cellosolve,methylacetate or the like and dispersing therein about 5% to 10% byweight of a nonionic surfactant such as an alkylphenoxy polyethoxyalcohol. This concentrate is dispersed in water for application as aliquid spray.

When the compounds of the invention are to be used as herbicides wheresoil treatments are involved, the compounds may be prepared and appliedas granular products. Preparation of the granular product can beachieved by dissolving the active compound in a solvent such asmethylene chloride, N-methylpyrrolidone or the like and spraying thethus prepared solution on a granular carrier such as corncob grits,sand, attapulgite, kaolin or the like.

The granular product thus prepared generally comprises about 3% to 20%by weight of the active ingredient and about 97% to 80% by weight of thegranular carrier.

In order to facilitate a further understanding of the invention, thefollowing non-limiting examples are presented primarily for the purposeof illustrating certain more specific details thereof. Unless otherwisenoted, all parts are by weight.

EXAMPLE 1 Preparation of 2-N-acetyl-2,3-dimethylbutyramide ##STR10##

2-Amino-2,3-dimethylbutyramide (114.8 g, 0.88 mols) is added to astirred solution of 120 mL of acetic anhydride in 200 mL of THF cooledto -20° C. under nitrogen at such a rate that temperature remains at-20° C. Upon completion of the addition the reaction mixture is allowedto warm to room temperature and then stir for 18 hours. The titleproduct precipitates as a white solid, which is filtered off and washedwith ether to yield 140.2 g of 2-N-acetyl-2,3-dimethylbutyramide havingamp of 114°-118° C.

EXAMPLE 2 Preparation of 2,4-dimethyl-4-isopropyl-1,3-imidazolin-5-one##STR11##

2-N-Acetyl-2,3-dimethylbutyramide (70 g) in 600 mL of aqueous NaOH (10%)is heated at 60°-70° C. (under N2) for two hours. The reaction mixtureis cooled with ice, and the pH adjusted to 5, first with conc. HCl andthen with 10% HCl. The acidified solution is extracted with ethylacetate several times affording 46 g of the title product after removalof the solvent. Concentration of the mother liquors by evaporation andextraction with ethyl acetate affords an additional 9.9 g of product.The isolated 2,4-dimethyl-4-isopropyl-1,3-imidazolin-4-one has a mp107°-109° C.

EXAMPLE 3 Preparation of 5-methyl-5-isopropyl-1,3-imidazolin-4-one##STR12##

A solution of 2-amino-2,3-dimethylbutyramide (130 g, 1 mol) andtriethylorthoformate (183 mL 1.1 mol) in 850 mL Of xylenes is heated toreflux using mechanical stirring, and a Dean-Stark trap to collectethanol. After three hours and 30 minutes no more ethanol is eliminated,and the reaction mixture is allowed to attain 50° C. The mixture isconcentrated to 1/3 of the volume and is then allowed to stand for 18hours. The title product precipitates as a white solid which iscollected by filtration (119.6 g), having mp 101°-104° C.

EXAMPLE 4 Preparation of 2,4-dimethyl-4-isopropyl-1,3-imidazolin-5-one##STR13##

A solution of 2-amino-2,3-dimethylbutyramide (100 g) andtriethylorthoacetate (125 g) in xylenes (500 mL) is heated at reflux(105°-138° C.) under a Dean-Stark trap. After six hours, 200 mLdistillate is collected at a pot temperature of 138° C. and only xylenewas present in the distillate. The reaction mixture is cooled andconcentrated in vacuo to 150 g thick light yellow oil. Hexanes is addedand the resulting solid filtered off to yield the 96.7 g (81.6%) of thetitle product having mp 107°-110° C.

Utilizing the above procedure and substituting(S)-2-amino-2,3-dimethylbutyramide (m.p. 78°-80° C. [α]_(D) ²⁵ -71°(THF)) affords (S)-2,4-dimethyl-4-isopropyl-1,3-imidazolin-5-one, m.p.93°-97° C., [α]_(D) ²⁵ -53° (THF) .

EXAMPLE 5 Preparation of1-(n-methylbenzenesulfonyl)-2,4-dimethyl-4-isopropyl-1,3-imidazolin-5-one##STR14##

p-Toluenesulfonyl chloride (2.47 g, 12.97 mol) is added to a stirredsolution of 2,4-dimethyl-4-isopropyl-1,3-imidazolin-5-one (2 g, 12.97mol) in 40 mL of dry methylene chloride and 1.4 molar equivalents of drypyridine, cooled with an ice bath and under nitrogen. The reactionmixture is allowed to warm to room temperature and then stir for 16hours. The reaction mixture is rapidly washed twice with water, oncewith HCl 10% , once with water, and dried over Na₂ SO₄. Evaporation ofthe methylene chloride solution affords 2.97 g of a yellow oil, which ispurified using a silica gel column eluting with CH₃ CN/hexanes/CH₂ Cl₂(1:3:6) yielding 1.95 g of solid; recrystallization from CH₂ C₂/ether/hexanes affords 1.37 g of the title product as a white solid,having mp 78°-80° C.

Utilizing the above procedure yields the formula I compounds listed inTable I below.

                  TABLE I                                                         ______________________________________                                         ##STR15##                                                                    Example                                                                              A      Q             R.sub.1                                                                            R.sub.2                                                                             mp °C.                          ______________________________________                                        5a     CH.sub.3                                                                              ##STR16##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                            78-80                                 5b     CH.sub.3                                                                              ##STR17##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                            82-83.5                               5c     CH.sub.3                                                                              ##STR18##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                           159-160                                5d     CH.sub.3                                                                              ##STR19##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                           121-123                                5e     CH.sub.3                                                                              ##STR20##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                            96-98                                  5f    CH.sub.3                                                                              ##STR21##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                            85-86                                 5g     CH.sub.3                                                                              ##STR22##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                           115-118                                5h     CH.sub.3                                                                              ##STR23##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                           103-104 (S)-(-) [α].sub.D.sup                                           .25 = -36.41                            5i    CH.sub.3                                                                              ##STR24##    CH.sub.3                                                                            .sub.- i-C.sub.3 H.sub.7                                                           123-125                                ______________________________________                                    

EXAMPLE 6 Preparation of2-acetamido-2,3-dimethyl-N-(D-toluenesulfonyl)butyramide-Method A##STR25##

p-Toluenesulfonyl chloride (2.4 g, 12.97 mmol) is added to a stirredsolution of 2,4-dimethyl-4-isopropyl-1,3-imidazolin-5-one in 40 mL ofmethylene chloride and 1.44 g of pyridine, cooled to -10° C. under N₂.Then the reaction mixture is allowed to warm to room temperature andstir for 16 hours.

The reaction mixture is checked for completeness of formation of4-isopropyl-2,4-dimethyl-1-(p-tolylsulfonyl)-2-imidazolin-5-one byinfrared spectroscopy. The product imidazolin-5-one is then hydrolyzedby diluting the solution with 100 mL of methylene chloride and washingtwice with water and once with HCl 10%. The organic layer isconcentrated in vacuo and the resulting yellowish oily residue is shakenwith ether and allowed to stand. Upon standing the title productprecipitates as a white solid, which after filtration,washing and dryinghas amp of 202°-203° C.

Utilizing the above procedure with the appropriate sulfonyl chloride andstarting imidazolinone yields the formula I herbicidal2-imidazolin-5-one intermediates and herbicidal formula II compoundslisted in Table II below.

                                      TABLE II                                    __________________________________________________________________________     ##STR26##                                                                               Formula I           Formula II                                     Formula VI              Means of                                                                             Compound                                                                            Formula II                               A   R.sub.1                                                                          R.sub.2                                                                           Q            Identification                                                                       mp °C.                                                                       Example                                  __________________________________________________________________________    CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          -p-tolyl    IR     202-203                                                                             6a.sub.1                                 H   CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-chlorophenyl                                                                             IR     186-187                                                                             6b.sub.1                                 H   CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chlorophenyl                                                                             IR     142-145                                                                             6c.sub.1                                 H   CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          -p-tolyl    IR     131-135                                                                             6d.sub.1                                                                sint gum                                       CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          -o-carbomethoxy                                                                           IR     157-160                                                                             6e.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-methoxyphenyl                                                                            IR     176-179                                                                             6f.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-nitrophenyl                                                                              IR     204-206                                                                             6g.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-chlorophenyl                                                                             IR     192-194                                                                             6h.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         phenyl       IR     170-172                                                                             6i.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chlorophenyl                                                                             IR     187-188                                                                             6j.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-nitrophenyl                                                                              IR     211-213                                                                             6k.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chloro-3-nitrophenyl                                                                     IR     209-210                                                                             6l.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-fluorophenyl                                                                             IR     183-184                                                                             6m.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          -p-tolyl    IR     201-203                                                                             6n.sub.1                                                                S                                                                             [α].sub.D.sup.25 =                                                      +36.62                                         CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3-nitrophenyl                                                                              IR     196-198                                                                             6o.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chlorophenyl                                                                             IR     202-203                                                                             6p.sub.1                                                                R                                                                             [α].sub.D.sup.25 =                                                      -25.98                                         CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          -o-tolyl    IR     195-199                                                                             6q.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3,4-dichlorophenyl                                                                         IR     204-206                                                                             6r.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,5-dichlorophenyl                                                                         IR     208-210                                                                             6s.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,3,4-trichlorophenyl                                                                      IR     222-223                                                                             6t.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,4,5-trichlorophenyl                                                                      IR     206-207                                                                             6u.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4- .sub.- t-butylphenyl                                                                    IR     167-171                                                                             6v.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,4-xylyl    IR     212-214                                                                             6w.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,3,5,6-tetramethyl-                                                                       IR     185-187                                                                             6x.sub.1                                            phenyl                                                             CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-iodophenyl IR     185-187                                                                             6y.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-acetamidophenyl                                                                          IR     218-222                                                                             6z.sub.1                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         (mesityl) 2,4,6-tri-                                                                       IR     192-194                                                                             6a.sub.2                                            methylphenyl                                                       CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,4-dinitrophenyl                                                                          IR     158-160                                                                             6b.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-bromophenyl                                                                              IR     190-193                                                                             6c.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-naphthyl   IR     165-170                                                                             6d.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         pentafluorophenyl                                                                          IR     200-202                                                                             6e.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          ##STR27##   IR     184-188                                                                             6f.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chloro-3-trifluoro-                                                                      IR     192-195                                                                             6g.sub.2                                            methylphenyl 2                                                     CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,5-xylyl    IR     197-198                                                                             6h.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3-trifluoromethyl-                                                                         IR     153-163                                                                             6i.sub.2                                            phenyl                                                             CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-trifluoromethyl-                                                                         IR     186-194                                                                             6j.sub.2                                            phenyl                                                             CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chlorophenyl                                                                             IR     197-200                                                                             6k.sub.2                                                                S +                                                                           [ ].sub.D.sup.25 =                                                            +24.91                                         CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-trifluoromethylphenyl                                                                    IR     186-190                                                                             6l.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-ethylphenyl                                                                              IR     186-189                                                                             6m.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chloro- -o-tolyl                                                                         IR     215-216                                                                             6n.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-cyanophenyl                                                                              IR     209-212                                                                             6o.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-carboxymethoxyphenyl                                                                     IR     159-160                                                                             6p.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-biphenyl   IR     170-174                                                                             6q.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-trifluoromethoxy-                                                                        IR     156-166                                                                             6r.sub.2                                            phenyl                                                             CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-carboxyphenyl                                                                            IR     179-180                                                                             6s.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,4-dichlorophenyl                                                                         IR     214-216                                                                             6t.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         1-naphthyl   IR     192-196                                                                             6u.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                          .sub.-- m-tolyl                                                                           IR     194-199                                                                             6v.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3-chlorophenyl                                                                             IR     160-164                                                                             6w.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,4-difluorophenyl                                                                         IR     190-193                                                                             6x.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-fluoro-3,5-xylyl                                                                         IR     180-185                                                                             6y.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3,5-dichlorophenyl                                                                         IR     190-195                                                                             6z.sub.2                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-acetoxyphenyl                                                                            IR     175-180                                                                             6a.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub. 3 H.sub.7                                                        4-chloro-2-trifluoro-                                                                      IR     206-208                                                                             6b.sub.3                                            methylphenyl                                                       CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,4-dibromophenyl                                                                          IR     208-210                                                                             6c.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chloro-2-cyanophenyl                                                                     IR     184-186                                                                             6d.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3,5-dichloro-2-hydroxy-                                                                    IR     169-171                                                                             6e.sub.3                                            phenyl                                                             CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4,6-dichloro- .sub.-- m-tolyl                                                              IR     225-226                                                                             6f.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-aminophenyl mono-                                                                        IR     204-206                                                                             6g.sub.3                                            hydrate                                                            CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3-chloro-4-fluorophenyl                                                                    IR     196-202                                                                             6h.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-vinylphenyl                                                                              IR     165-172                                                                             6i.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         5-bromo-2-methoxyphenyl                                                                    IR     208-211                                                                             6j.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-acetylphenyl                                                                             IR     179-183                                                                             6k.sub.3                                 OCH.sub.3                                                                         CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-chlorophenyl                                                                             IR     134-135                                                                             6l.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-fluoro- -o-tolyl                                                                         IR     206-210                                                                             6m.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-chloro- -p-tolyl                                                                         IR     210-213                                                                             6n.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         3-bromophenyl                                                                              IR     200-202                                                                             6o.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         6-chloro- -o-tolyl                                                                         IR     222-225                                                                             6p.sub.3                                 CH.sub.3                                                                          C.sub.2 H.sub.5                                                                  C.sub.2 H.sub.5                                                                    -p-tolyl    IR     180-181                                                                             6q.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                         C.sub.2 H.sub.5                                                                    -p-tolyl    IR     170-174                                                                             6r.sub.3                                 CH.sub.3                                                                          C.sub.2 H.sub.5                                                                   .sub.- i-C.sub.3 H.sub.7                                                          -p-tolyl    IR     145-147                                                                             6s.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                         cyclo-                                                                             -p-tolyl    IR     187-188                                                                             6t.sub.3                                        propyl                                                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,6-dichlorophenyl                                                                         IR     219-220                                                                             6u.sub.3                                 CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         4-bromo-2,5-difluoro-                                                                      IR     229-222                                                                             6v.sub.3                                            phenyl                                                             CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2-chloro-5-trifluoro-                                                                      IR     195-198                                                                             6w.sub.3                                            methylphenyl                                                       CH.sub.3                                                                          CH.sub.3                                                                          .sub.- i-C.sub.3 H.sub.7                                                         2,5-dibromo-3,6-                                                                           IR     197-198                                                                             6x.sub.3                                            difluorophenyl                                                     __________________________________________________________________________

EXAMPLE 7 Preparation of2-formamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide ##STR28##

p-Toluenesulfonyl chloride (153.42 g, 0.0815 mol) is added to a stirredsolution of 4-methyl-4-isopropyl-1,3-imidazolin-5-one, (112 g, 0.815mol) in 1200 mL of methylene chloride, cooled to -12° C. under anitrogen atmosphere. Pyridine (91 mL) is then added, and the reactionmixture is allowed to stir at -10° C. for three hours and then allowedto attain room temperature. The completeness of formation of theintermediate imidazolinone is determined by IR. The intermediateimidazolinone is hydrolyzed by washing the reaction mixture once with500 mL of aqueous HCl 10%, and once with water. The two-layer mixture isallowed to stand for 30 minutes and the resulting white solid filteredoff and washed with ether, to yield 217.65 g of the title product as awhite solid having mp 131°-135° C.

Substitution of p-chlorobenzenesulfonyl chloride for p-toluenesulfonylchloride above affords2-formamido-2,3-dimethyl-N-(p-chlorobenzenesulfonyl)butyramide, mp142°-145° C.

EXAMPLE 8 Preparation of2-amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride##STR29##

A suspension of 2-formamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide(99.4 g, 0.318 mols) in 500 mL of methanol, 500 mL of water, and 500 mLof aqueous HCl 10% is heated at 80° C. until all the solid has dissolved(one hour). The reaction mixture is concentrated to 1/3 of the volumeand the resulting precipitate is filtered off. After drying the titleproduct is obtained as a white solid, having mp 161°-165° C.

Substitution of2-formamido-2,3-dimethyl-N-(p-chlorobenzenesulfonyl)butyramide, affords2-amino-2,3-dimethyl-N-(p-chlorobenzenesulfonyl)butyramidehydrochloride, mp 170°-172° C.

EXAMPLE 9 Preparation of2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide--Method B##STR30##

2-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride (45 g˜0.4 mols) is completely dissolved in 160 mL of pyridine and 500 mL ofTHF is added. Acetic anhydride (45 mL) is then poured into the solutionand the reaction mixture is heated at reflux for one hour. The solventsare removed under reduced pressure, and the oily residue is crystallizedfrom EtOH/water affording 33.09 g of the title product having m.p.198°-199° C.

EXAMPLE 10a Preparation of2,3-dimethyl-2-propionamido-N-(p-tolylsulfonyl)butyramide ##STR31##

2-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride (1.2 g,5.3 mol) is dissolved in 25 mL of toluene under N₂. Then triethylamine(1.9 mL, 2.5 equivalents) is added, followed by immediate addition ofpropionyl chloride (0.55 mL, 6.36 mol). The reaction mixture is heatedfor one hour, and then solvents are removed under reduced pressure. Theyellowish residue is recrystallized from EtOH/water, to yield the titleproduct as a white solid having mp 166°-168° C.

Utilizing the above procedure with different acid chlorides yields theherbicidal formula II compounds listed in Table III below.

                  TABLE III                                                       ______________________________________                                         ##STR32##                                                                    Example   A                R.sub.5                                                                              mp °C.                               ______________________________________                                        10b       C.sub.2 H.sub.5  CH.sub.3                                                                             166-168                                     c         CH(CH.sub.3).sub.2                                                                             CH.sub.3                                                                             172-174                                     d         n-C.sub.4 H.sub.9                                                                              CH.sub.3                                                                             165-168                                     e         CH.sub.2 OCH.sub.3                                                                             CH.sub.3                                                                             165-167                                     f         CH.sub.2 CH(CH.sub.3).sub.2                                                                    CH.sub.3                                                                             174-176                                     g         C.sub.3 H.sub.7  CH.sub.3                                                                             188-190                                     h         CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                             186-191                                     i         CHCHCH.sub.3     CH.sub.3                                                                             194-197                                                ##STR33##       CH.sub.3                                                                             208-212                                     k         CHCH.sub.2       CH.sub.3                                                                             180-182                                     l         CH.sub.2 COOCH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                             162-165                                     m                                                                                        ##STR34##       CH.sub.3                                                                             139-149                                     n         CHCH.sub.2       Cl     165-166                                     o         CHCHCH.sub.3     Cl     177-180                                     10p                                                                                      ##STR35##       Cl     164-167                                     q         CH.sub.2 CH.sub.2 Cl                                                                           CH.sub.3                                                                             --                                          r         SCH.sub.3        CH.sub.3                                                                             --                                          s         SOCH.sub.3       CH.sub.3                                                                             --                                          t         SO.sub.2 CH.sub.3                                                                              CH.sub.3                                                                             --                                          u         phenyl           CH.sub.3                                                                             --                                          v         CHCHCl           CH.sub.3                                                                             --                                          w         CClCHCl          CH.sub.3                                                                             --                                          x         CHCLCH.sub.2 Cl  CH.sub.3                                                                             --                                          y                                                                                        ##STR36##       CH.sub.3                                                                             --                                          z         CF.sub.3         CH.sub.3                                                                             --                                          ______________________________________                                    

EXAMPLE 11a Preparation of1-{1,2-dimethyl-1-[(p-tolylsulfonyl)carbamoyl]propyl}-3-methylurea##STR37##

A solution of 2-amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramidehydrochloride (5 g, 15.58 mmols) dissolved in 50 mL of DMF undernitrogen is cooled to -30° C. Then 10 mL of methyl isocyanate in 10 mLof THF is added at such a rate that temperature is maintained at -30°C., and the reaction mixture is allowed to stir for two hours at -30° C.and then for 16 hours at room temperature.

The THF is removed by concentration in vacuo and water is added. Thewhite solid which precipitates is filtered off and dried to yield thetitle product, 1.5 g, having mp 170°-171° C.

Utilizing the above procedure with different 1-sulfonylcarbamoylaminesand isocyanates yields the formula II compounds listed in Table IVbelow.

                  TABLE IV                                                        ______________________________________                                         ##STR38##                                                                    Example   A                R.sub.5                                                                              mp °C.                               ______________________________________                                        11b       NHCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          CH.sub.3                                                                             160-162                                     c         NHCH(CH.sub.3).sub.2                                                                           CH.sub.3                                                                             175-178                                                ##STR39##       CH.sub.3                                                                             172-174                                     e         NHCH.sub.2 CH.sub.2 Cl                                                                         CH.sub.3                                                                             172-173                                     f         NHCH.sub.2 CHCH.sub.2                                                                          CH.sub.3                                                                             167-169                                     g         NHCH.sub.2 CH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                             163-165                                     h                                                                                        ##STR40##       CH.sub.3                                                                             210-212                                     i                                                                                        ##STR41##       CH.sub.3                                                                             167-168                                     j         NHCH.sub.3       Cl     159-160                                     ______________________________________                                    

EXAMPLE 12 Preparation of the zwitterion of2-amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide ##STR42##

2-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride (20 g,62.34 mmol) is dissolved in 100 mL of water and 50 mL of ethanol.Triethylamine is then added until the pH of the reaction mixture isapproximately 11, and the resulting solution is stirred for one hour.

The pH of the reaction mixture is adjusted to pH 6 with 10% aqueous HCland the resulting white precipitate is filtered off, washed with water,and dried to yield the title compound as a white solid having mp262°-265° C.

Utilizing the above procedure and substituting sodium bicarbonate fortriethylamine also yields the desired zwitterion.

EXAMPLE 13 Preparation of1-{1,2-dimethyl-[(p-tolylsulfonyl)carbamoyl]propyl}-3-methylurea##STR43##

Methyl isocyanate (0.42 g, 4.22 mmol) is added to a stirred solutioncontaining 1 g (3.52 mmoles) of the zwitterion of2-amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide in 10 mL of dry DMF(dried over dessicant), under a nitrogen atmosphere, cooled at -20° C.in dry-ice/acetone bath. Then the temperature of the reaction mixture isallowed to attain room temperature and stir for one hour. Water (10 mL)is added and the product precipitates as a white solid, which isfiltered off, washed with water, and dried, to afford 0.6 g of the titlecompound as a white solid which upon crystallization from DMF/water hasmp 120°-125° C.

EXAMPLE 14 Preparation of2-acetamido-2,3-dimethyl-N-)p-tolylsulfonyl)butyramide ##STR44##

Sodium hydride (0.51 g, 60%) is added to a stirred solution of2-N-acetyl-2,3-dimethylbutyramide (2 g, 11.6 mmols) in 40 mL of dry THFand 20 mL of dry methylene chloride under a nitrogen atmosphere, cooledto -20° C. with a dry-ice/acetone bath. When no more bubbles evolve,2.21 g of p-toluenesulfonyl chloride is added and the temperature of thereaction mixture is allowed to attain room temperature and then stir fortwo hours, maintaining the temperature with a water bath (reaction isexothermic). Then 100 mL each of methylene chloride and aqueous sodiumbicarbonate is added. The resulting aqueous solution is washed withmethylene chloride, filtered, and the filtrate acidified to pH 2. Thetitle compound precipitates as a white solid, which after filtration anddrying affords 1.5 g as a white solid having mp 200°-204° C.

EXAMPLE 15 Preparation of 2,4-dimethyl-4-isopropyl-2-oxazolin-5-one##STR45##

2-Acetamido-2,3-dimethylbutyric acid (16 g) is dissolved in THF (200 mL)and dicyclohexylcarbodiimide (DCC, 21.0 g) is added. The mixture isallowed to stir for 16 hours at 25° C. At the end of this time themixture is filtered and evaporated to dryness. The residue is dissolvedin CH₂ Cl₂ (10 mL) and filtered again. Evaporation of the filtrate givesthe crude product which is purified by distillation at 0.65 mmHg, havingbp 50° C.

EXAMPLE 16 Preparation of2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide ##STR46##

2,4-Dimethyl-4-isopropyl-2-oxazolin-5-one (2.0 g) is mixed with DMF (50mL), THF (70 mL) and sodium p-toluene sulfonamide (5.0 g), and theresulting mixture is heated at reflux for 16 hours. At the end of thistime the mixture is cooled, and the solvents are removed under vacuum.The residue is mixed with water and the pH adjusted to 8 with NaHCO₃.The aqueous mixture is extracted with ethyl acetate and the organiclayers are discarded. The aqueous mixture is acidified to pH24 with HCland saturated with NaCl and extracted with ethyl acetate. The organicextracts are combined, dried over MgSO₄, filtered and evaporated to give0.66 of the title product.

EXAMPLE 16a Preparation of2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide ##STR47##

2-Acetamido-2,3-dimethylbutyric acid (1.5 g) is dissolved in a solutionof triethylamine (2.7 g) in diethyl ether (50 mL) and cooled to 0° C.;ethylchloroformate (1.1 g) is added dropwise and the mixture is stirredat 0° to room temperature over one hour. The mixture is filtered, andthe filtrate is concentrated in vacuo to afford the oily mixed anhydride(1.5 g). This material is mixed with 3 g of p-toluenesulfonamide, sodiumsalt, in 25 mL dimethylformamide, and the resulting mixture is heated at80° C. for 16 hours. The reaction is cooled, concentrated in vacuo, andthe residue is partitioned between methylene chloride and saturated,aqueous sodium bicarbonate. Acidification of the aqueous layer withconc. HCl to pH 1, extraction with CH₂ Cl₂, drying, and stripping theorganic phase affords the title product (3.3 g).

EXAMPLE 17 Preparation of5-isopropyl-5-methyl-3-(p-tolylsulfonyl)hydantoin and5-isopropyl-5-methyl, 1,3-bis(p-tolylsulfonyl)hydantoin ##STR48##

p-Toluenesulfonyl chloride (12.21 g) in 10 mL THF is added to a stirredmixture of 5-isopropyl-5-methyl hydantoin (10 g, 0.064 mol) and sodiumhydride (2.56 g) in 90 mL THF and the reaction mixture is allowed tostir under a nitrogen atmosphere for 16 hours. The reaction mixture isfiltered and the filtrate concentrated to a tan oil 14.2 g. A thin layerchromatograph of the mixture on silica gel with 10% CH₃ CN/CH₂ Cl₂eluant showed two products which are separated by column chromatographyon silica gel with 10% CH₃ CN/CH₂ C₁₂ as eluant to give

Fraction 1, 5-isopropyl-5-methyl-1,3-bis(p-tolylsulfonyl)hydantoin (2.1g) having mp 144°-146° C. and

Fraction 2, 5-isopropyl-5-methyl-3-(p-tolylsulfonyl)hydantoin (7.2 g)having mp 102°-103° C.

EXAMPLE 18 Preparation of methylamine salt of1-{1{[p-chlorophenyl)sulfonyl]carbamoyl}-1,2-dimethylpropyl}-3-methylurea

A mixture of 5-isopropyl-5-methyl-3-(p-chlorosulfonyl)hydantoin (2.0 g)and methylamine (10 mL, 40% aqueous solution) in tetrahydrofuran (THF,50 mL) is allowed to stir at room temperature for 16 hours. The reactionmixture is concentrated under reduced pressure and the resulting residuedissolved in water and filtered. The filtrate is acidified to pH 3 andthe resulting solid collected by filtration. The solid, 1.4 g, isdissolved in THF (50 mL) and methylamine (10 mL, 40%) is added. Themixture is stirred for one hour and then concentrated under reducedpressure to yield the title product (1.3 g) as a white solid having mp120°-122° C.

By utilizing the above procedure and substituting the appropriatelysubstituted hydantoin and methanol as reactants, methyl(1,2-dimethyl-1-[(p-tolylsulfonyl)carbamoyl]propyl}carbamate having mp120°-122° C. is obtained, and by substituting 1,1-dimethylhydrazine formethylamine yields4-(1,2-dimethyl-1-[(p-tolylsulfonyl)carbamoyl]propyl)-1,1-dimethylsemicarbazidehaving m.p. 96°-98° C.

EXAMPLE 19 Preparation of isopropylamine salt of2-acetamido-N-[4-chloro-o-tolyl)sulfonyl]-2,3-dimethylbutyramide##STR49##

A solution of 1.0 g (2.8 mmols) of2-acetamido-N-[(4-chloro-o-tolyl)sulfonyl]-2,3-dimethylbutyramide in 50mL of THF at 25° C. is treated with 0.17 g (2.9 mmols) ofisopropylamine. The resulting mixture is stirred at 25° C. for one hour,after which the solution is diluted with 50 mL diethyl ether. Theresulting suspension is stirred for 15 minutes, and the solid whichforms is collected by filtration. This solid is washed with two 50 mLportions of warm THF and air dried to afford 0.97 g (84%) of the titleproduct as a beige solid having mp 161°-163° C.

EXAMPLE 20 Preparation of sodium salt of2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide ##STR50##

Solid NaH (0.24 g, of 50% NaH, 0.005 mols) is added all at once to astirred solution of2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide (1.63 g, 0.005mols) in 20 mL THF. Stirring is continued for one hour and the resultingwhite solid is filtered and dried to give the title product (1.36 g,78.1%) having mp 167°-169° C.

EXAMPLE 21

Utilizing the above procedures described in examples 17-19 yields thesalts listed in Table V below.

                  TABLE V                                                         ______________________________________                                         ##STR51##                                                                    Example A      Q           Salt       mp °C.                           ______________________________________                                        21a     CH.sub.3                                                                              -p-tolyl   isopropylamine                                                                           144-146                                 21b     CH.sub.3                                                                             4-chlorophenyl                                                                            isopropylamine                                                                           182-184                                 21c     CH.sub.3                                                                             4,6-dichloro-                                                                             isopropylamine                                                                           176-181                                                 .sub.-- m-tolyl                                               21d     CH.sub.3                                                                             5-dimethyl- isopropylamine                                                                            88-128                                                amino-1-                                                                      naphthyl                                                       ______________________________________                                    

EXAMPLE 22

Post-emergence herbicidal evaluation of test compounds

The postemergence herbicidal activity of the compounds of the presentinvention is demonstrated by the following tests, wherein a variety ofmonocotyledonous and dicotyledonous plants are treated with testcompounds dispersed in aqueous acetone mixtures. In the tests, seedlingplants are grown in jiffy flats for about two weeks. The test compoundsare dispersed in 50 acetone/water mixtures containing 0.5% TWEEN 20, apolyoxyethylene sorbitan monolaurate surfactant of Atlas ChemicalIndustries, in sufficient quantity to provide the equivalent of about0.032 kg to 8 kg per hectare of active compound when applied to theplants through a spray nozzle operating at 40 psi for a predeterminedtime. After spraying, the plants are placed on greenhouse benches andare cared for in the usual manner, commensurate with conventionalgreenhouse practices. From four to five weeks after treatment, theseedling plants, are examined and rated according to the rating systemprovided below. The data obtained are recorded in Table VI below.

    ______________________________________                                                           % Difference in growth                                     Rating system      from the check*                                            ______________________________________                                        0 - No effect      0                                                          1 - Possible effect                                                                               1-10                                                      2 - Slight effect  11-25                                                      3 - Moderate effect                                                                              26-40                                                      5 - Definite injury                                                                              41-60                                                      6 - Herbicidal effect                                                                            61-75                                                      7 - Good herbicidal effect                                                                       76-90                                                      8 - Approaching complete kill                                                                    91-99                                                      9 - Complete kill  100                                                        4 - Abnormal growth, that is, a definite physiological                          malformation but with an over-all effect less than                            a 5 on the rating scale.                                                    ______________________________________                                    

In most cases the data are for a single test, but in several instances,they are average values obtained from more than one test.

    ______________________________________                                        Plant Species Used                                                            Abbreviation                                                                             Common Name   Scientific Name                                      ______________________________________                                        BARNYARDGR Barnyardgrass Echinochloa crus-galli                                                        (L) Beau                                             FOXTAIL SP Foxtail, Spp. Setaria Spp.                                         P NUTSEDGE Nutsedge, Purple                                                                            Cyperus rotundus, L.                                 WILD OATS  Oat, Wild     Avena fatua, L.                                      QUACKGRASS Quackgrass    Agropyron repens,                                                             (L) Beauv.                                           FLD bindwd Bindweed, Field                                                                             Convolvulus arvensis,                                           (Rhizome)     L.                                                   MATRIC SPP Matricaria Spp.                                                                             Matricaria Spp.                                      MRNGLRY SP Morningglory Spp.                                                                           Ipomoea Spp.                                         WILD MUST  Mustard, Wild Brassica kaber,                                                               (DC) L.C. Wheelr                                     RAGWEED    Ragweed, Common                                                                             Ambrosia artemisiifolia                                                       L.                                                   VELVETLEAF Velvetleaf    Abutilon theophrasti,                                                         medic.                                               ______________________________________                                    

                                      TABLE VI                                    __________________________________________________________________________    POST-EMERGENCE TESTS - RATES IN KG/HA                                         __________________________________________________________________________    Com-                                                                          pound                                                                         of       BARNY                                                                              FOXTA                                                                              P NUT                                                                              WILD                                                                              QUACK                                                                              FLD B                                                                              MATRI                                                                              MRNGL                                                                              WILD RAG  VELVE               Example                                                                            RATE                                                                              ARDGR                                                                              IL SP                                                                              SEDGE                                                                              OATS                                                                              GRASS                                                                              INDWD                                                                              C SPP                                                                              RY SP                                                                              MUSTD                                                                              WEED TLEAF               __________________________________________________________________________    5a   2.000         0.0      0.0       3.0  0.0  0.0  0.0  1.0                      1.500         0.0      0.0       2.0  0.0  0.0  0.0  4.0                      1.000                                                                             0.0  3.0  1.5  0.0 1.0  6.0  2.0  3.0  0.0  3.5  4.5                       .750         0.0      0.0       1.0  0.0  0.0  0.0  0.0                       .500                                                                             0.0  1.0  0.5  0.0 0.5  4.0  1.0  1.0  0.0  4.0  4.5                 5b   4.000                                                                             6.0  9.0  9.0  9.0 9.0  9.0       9.0  9.0       9.0                      2.000                                                                             6.0  9.0  9.0  9.0 9.0  9.0       9.0  9.0       9.0                      1.000                                                                             4.0  7.0  9.0  9.0 9.0  7.0       9.0  9.0       9.0                       .500                                                                             2.0  7.0  4.0  6.0 8.0  6.0       9.0  9.0       9.0                 5d   4.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       7.0  9.0  3.0  1.0                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       7.0  8.0  2.0  1.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       8.0  8.0  3.0  0.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       4.0  7.0  0.0  0.0                 5e   4.000                                                                             3.5  9.0  3.0  8.5 8.5  3.0       7.5  8.5  8.5  6.0                      2.000                                                                             7.0  6.0  4.0  9.0 9.0  6.0       9.0  9.0  8.0  9.0                      1.000                                                                             7.0  6.0  1.0  9.0 9.0  4.0       7.0  9.0  9.0  9.0                       .500                                                                             3.0  1.0  0.0  4.0 7.0  3.0       7.0  9.0  8.0  7.0                 5f   4.000                                                                             1.0  1.0  4.0  1.0 2.0  8.0       9.0  9.0  8.0  9.0                      2.000                                                                             0.0  0.0  3.0  0.0 1.0  6.0       9.0  9.0  8.0  9.0                      1.000                                                                             0.0  0.0  1.0  0.0      6.0       9.0  7.0  8.0  9.0                       .500                                                                             0.0  0.0  1.0  0.0 0.0  6.0       9.0  9.0  6.0  9.0                 5g   4.000                                                                             0.0  0.0  3.0  0.0 2.0  4.0       7.0  7.0  6.0  7.0                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  2.0       7.0  7.0  5.0  5.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0            3.0  5.0  4.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  2.0       3.0  3.0  0.0  1.0                 5h   1.000                                                                             0.0  0.0  4.0  0.0 0.0  8.0       8.0  9.0  8.0  9.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  6.0       7.0  9.0  7.0  8.0                 6a.sub.1                                                                           4.000                                                                             2.8  3.5  5.5  1.6 3.5  7.3       6.0  9.0  8.3  9.0                      2.000                                                                             1.7  2.8  3.0  0.8 2.7  5.9  8.3  4.8  8.1  6.8  8.4                      1.500         0.0      0.0       5.0  0.0  0.0  0.0  1.0                      1.000                                                                             0.6  2.3  2.3  0.4 1.1  5.3  7.3  3.5  8.0  6.3  8.0                       .750         0.0  0.0 1.7       6.0  2.5  5.3  0.0  4.5                       .500                                                                             0.1  1.3  1.3  0.2 0.4  4.4  6.6  2.1  7.8  5.6  7.8                 6b.sub.1                                                                           1.000                                                                             0.0  0.0  0.0  0.0 0.0  3.0       2.0       2.0  1.5                       .500                                                                             0.0  0.0  0.0  0.0 0.0  3.0       1.0       1.0  0.5                 6c.sub.1                                                                           1.000                                                                             0.0  0.5  0.0  0.0 0.0  8.5       2.0       7.0  6.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  7.5       1.5       5.5  4.5                 6d.sub.1                                                                           4.000                                                                             0.0       0.0  1.0 0.0  9.0       2.0  1.0  5.0  4.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  7.0       1.0       6.0  4.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0            1.0       7.0  4.0                 6e.sub.1                                                                           1.000                                                                             0.0  0.0  0.0  0.0 0.5  4.5       4.0       2.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  4.0       1.5       1.0  2.0                 6g.sub.1                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       1.5       1.5  2.5                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.5       2.0  0.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.5       1.5  0.5                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.5       1.5  0.0                 6h.sub.1                                                                           4.000                                                                             3.0  6.0  0.0  5.0 4.0  9.0       8.0       9.0  9.0                      2.000                                                                             3.0  5.0  0.0  5.0 2.0  9.0       8.0       9.0  9.0                      1.000                                                                             2.0  2.0  0.0  2.0 2.0  8.0       7.0       8.0  9.0                       .500                                                                             0.0  1.0  0.0  2.0 1.0  7.0       7.0       8.0  7.0                 6i.sub.l                                                                           4.000                                                                             6.0  9.0  0.0  9.0 7.0  4.0       6.0       4.0  9.0                      2.000                                                                             3.0  9.0  0.0  5.0 6.0  4.0       3.0       2.0  9.0                      1.000                                                                             3.0  7.0  0.0  1.0 5.0  1.0       2.0       2.0  9.0                       .500                                                                             1.0  4.0  0.0  0.0 5.0  0.0       1.0       2.0  9.0                 6j.sub.1                                                                           4.000                                                                             7.3  7.8  7.2  8.8 7.8  8.2       8.0  9.0  8.8  9.0                      3.000                                                                             6.0  8.0  7.0  9.0 9.0  6.0       7.0  9.0  9.0  9.0                      2.000                                                                             6.2  7.6  6.8  8.2 7.5  8.6  9.0  7.9  9.0  8.6  9.0                      1.000                                                                             3.7  5.0  5.9  7.7 7.5  7.5  9.0  7.8  9.0  8.5  8.8                       .800                                                                             1.0  5.0  6.0  9.0 5.0  5.0       7.0  9.0       9.0                       .750         0.0      7.0            8.0  9.0  8.0  9.0                       .500                                                                             2.4  5.1  2.9  6.1 5.9  5.5  9.0  6.9  9.0  7.4  8.6                 6k.sub.1                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       0.0  8.0  6.0  4.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  7.0  5.0  1.0                 6l.sub.1                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  5.0       2.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  4.0  4.0  1.0                 6m.sub.1                                                                           4.000                                                                             9.0  9.0  8.0  6.0 6.0  9.0       9.0  9.0  8.0  9.0                      2.000                                                                             9.0  9.0  8.0  9.0 9.0  6.0       9.0  9.0  7.0  9.0                      1.000                                                                             6.7  9.0  2.7  8.5 8.0  7.0       7.0  9.0  8.0  9.0                       .500                                                                             4.8  6.7  1.3  8.0 6.3  5.3       6.8  9.0  6.0  9.0                 6n.sub.1                                                                           4.000                                                                             8.0  6.0  9.0  2.0 7.0  9.0       9.0  9.0       9.0                      3.000                                                                             6.0  6.0  7.0  2.0 7.0  8.0       8.0  9.0       9.0                      2.000                                                                             1.0  4.0  7.0  1.0 6.0  6.0       7.0  9.0       9.0                      1.000                                                                             0.0  3.0  6.0  0.0 6.0  4.0       6.0  9.0       9.0                       .800                                                                             0.0  2.0  4.0  0.0 5.0  4.0       2.0  9.0       9.0                       .500                                                                             0.0  1.0  2.0  0.0      4.0       1.0  9.0       9.0                 6o.sub.1                                                                           4.000                                                                             0.0  0.0  0.0  0.0 2.0  2.0       6.0  9.0  7.0  4.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       0.0  3.0  0.0  1.0                 6q.sub.1                                                                           4.000                                                                             0.0  0.0  2.0  0.0 0.0  6.0       8.0  9.0  8.5  9.0                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  6.0       8.0  9.0  7.0  9.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  4.0       2.0  9.0  7.0  7.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  3.0       4.7  9.0  6.0  7.0                 6r.sub.1                                                                           4.000                                                                             6.0  7.0  6.0  9.0 5.0  6.0       8.0  9.0  9.0  9.0                      1.000                                                                             3.0  2.0  2.0  2.0 1.0  3.0       4.0  9.0  8.0  8.0                       .500                                                                             0.5  0.0  0.5  0.5 1.5  2.5       2.5  9.0  7.5  6.0                 6s.sub.1                                                                           4.000                                                                             7.0  8.0  6.0  8.0 7.0  6.0       8.0  9.0  8.0  9.0                      1.000                                                                             7.0  1.0  0.0  0.0 3.0  3.0       8.0  9.0  7.0  8.0                       .500                                                                             4.0  1.0  0.0  0.0 1.5  4.5       7.0  9.0  7.0  7.5                 6t.sub.1                                                                           4.000                                                                             6.5  4.5  4.5  7.0 5.5  6.5       8.0  9.0  7.0  7.0                      2.000                                                                             3.0  2.0  0.0  3.0 5.0  5.0       7.0  9.0  7.0  7.0                      1.000                                                                             0.0  1.0  0.0  2.0 4.0  5.0       7.0  9.0  7.0  2.0                       .500                                                                             0.0  0.0  0.0  0.5 1.0  4.0       5.7  8.5  7.0  2.5                 6u.sub.1                                                                           4.000                                                                             0.0  0.0  3.0  0.0 0.0  8.0       8.0  9.0  8.0  9.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  2.0       2.5  9.0  5.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  3.5       3.3  8.5  6.5  3.5                 6v.sub.1                                                                           4.000                                                                             0.0  0.0       0.0 0.0  1.0       0.0  1.0  2.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  1.0  1.0  1.0                 6w.sub.1                                                                           4.000                                                                             0.0  1.5  3.5  0.0 0.5  9.0       8.0  9.0  6.0  9.0                      2.000                                                                             0.0  0.0  2.0  0.0 0.0  9.0       9.0  9.0  5.0  9.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  6.0       7.0  9.0  5.0  9.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  5.5       5.5  7.5  4.5  7.0                 6x.sub.1                                                                           4.000                                                                             0.0  0.0  2.0  0.0 0.0  0.0       6.0  7.0       5.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       3.0  4.0  0.0  2.0                 6y.sub.1                                                                           4.000                                                                             6.0  6.0  4.0  6.0 2.0  5.0       6.0  9.0  9.0  9.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  2.0       2.0  9.0       7.0                 6z.sub.1                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0  0.5  0.5  0.5                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  0.0  0.0  0.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  0.0  0.0  0.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.5  0.5  0.0  0.5                 6a.sub.2                                                                           4.000                                                                             0.0  0.0  5.0  0.0 0.0  9.0       8.0  8.0  0.0  7.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  4.0       6.0  5.0       4.0                 6b.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  0.0                           6c.sub.2                                                                           4.000                                                                             7.0  8.0  7.0  9.0 8.0  7.0       9.0  9.0  9.0  9.0                      1.000                                                                             3.0  5.0  0.0  2.0 2.0  2.0       5.0  9.0  8.0  8.0                       .500                                                                             1.5  3.5  1.5  3.0 1.0  3.5       5.5  9.0  8.0  8.0                 6d.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  5.0       1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       4.0  5.0       1.0                 6e.sub.2                                                                           4.000                                                                             1.0  0.0  1.0  1.0 0.0  1.0       4.0  6.0  8.0  4.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       2.0  7.0  7.0  1.0                 6f.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  0.0  2.0                            .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  2.0  3.0  1.0                 6g.sub.2                                                                           4.000                                                                             0.0  0.0  1.0  0.0 0.0  2.0       2.0  7.0  6.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0  4.0       1.0                 6h.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  2.0       4.0  5.0  5.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       2.0  6.0  1.0  2.0                 6i.sub.2                                                                           4.000                                                                             2.0  1.0  0.0  0.0 1.0  4.0       2.0  9.0  6.0  7.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0  8.0  5.0  5.0                 6j.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  2.0 2.0  3.0       7.0  9.0       7.0                      1.000                                                                             0.0       0.0                     0.0                                      .500                                                                             0.0  0.0  0.0  1.0 1.0  2.0       3.5  7.0       4.0                 6k.sub.2                                                                           4.000                                                                             9.0  9.0  8.0  9.0 9.0  7.0       8.0  9.0       9.0                      3.000                                                                             7.0  9.0  8.0  9.0 7.0  8.0       8.0  9.0  9.0  9.0                      2.000                                                                             6.0  6.0  6.0  9.0 8.0  5.0       9.0  9.0  9.0  9.0                      1.000                                                                             3.5  3.0  5.5  9.0 9.0  9.0       7.5  9.0       9.0                       .800                                                                             5.0  6.0  5.0  9.0 9.0  7.0       7.0  9.0       9.0                       .500                                                                             3.0  6.5  3.3  8.5 8.5  9.0       6.0  9.0  9.0  9.0                 61.sub.2                                                                           4.000                                                                             2.0  1.0  6.0  6.0 7.0  9.0       8.0  9.0  9.0  7.0                      1.000                                                                             0.0       0.0                     0.0                                      .500                                                                             0.0  0.0  0.0  0.0 2.0  7.0       3.0  8.0       5.0                 6m.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 1.0  2.0       2.0  4.0       2.0                       .500                                                                             0.0  0.0  0.0  0.0 1.0  0.0       2.0  4.0       1.0                 6n.sub.2                                                                           4.000                                                                             3.0  2.0  6.0  2.0 1.0  8.0       8.0  9.0       9.0                      2.000                                                                             0.0  2.0  5.0  0.0 1.5  7.0  9.0  8.0  9.0  8.0  7.5                      1.000                                                                             0.0  0.5  4.0  0.0 1.7  7.0  8.0  7.3  8.5  7.0  7.0                       .750              0.0 0.0       8.0  7.0  8.0  6.0  6.0                       .500                                                                             0.0  0.5  0.5  0.0 0.0  6.5  8.0  7.3  8.5  6.0  4.3                 6o.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 2.0  1.0       4.0  6.0  5.0  2.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  2.0       4.0  7.0  4.0                      6p.sub.2                                                                           4.000                                                                             0.0  0.0  1.0  0.0 1.0  1.0       0.0  0.0  0.0  0.0                 6r.sub.2                                                                           4.000                                                                             0.0  0.0  3.0  0.0 1.0  2.0       3.0  5.0       1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       2.0  4.0  7.0  1.0                 6s.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       1.0  1.0  0.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       1.0  1.0       1.0                 6t.sub.2                                                                           4.000                                                                             5.5  3.5  6.0  6.5 4.5  9.0       8.5  9.0  8.0  9.0                      2.000                                                                             5.0  3.0  2.5  5.0 0.5  8.5       7.5  9.0  8.0  8.5                      1.000                                                                             1.3  2.0  2.3  2.0 2.0  7.5       7.0  9.0  8.5  7.0                       .500                                                                             0.0  1.0  0.0  0.0 0.5  6.7       8.0  9.0  7.0  6.0                 6u.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  3.0       2.0  9.0  1.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       0.0  7.0  0.0  1.0                 6v.sub.2                                                                           4.000                                                                             0.0  2.0  2.0  0.0 0.0  4.0       3.0  9.0  6.0  8.0                       .500                                                                             0.0  1.0  0.0  0.0 0.0  1.0       1.0  6.0  0.0  6.0                 6w.sub.2                                                                           4.000                                                                             7.5  7.5  5.0  9.0 9.0  7.5       8.5  9.0  8.0  9.0                      2.000                                                                             2.0  5.0  0.0  9.0 8.0  5.0       8.0  9.0       9.0                      1.000                                                                             1.0  3.0  0.0  6.0 7.0  5.0       6.0  8.0  7.0  9.0                       .500                                                                             2.0  2.0  0.0  2.0 4.5  4.0       4.5  9.0  2.5  8.0                 6x.sub.2                                                                           4.000                                                                             8.5  9.0  9.0  9.0 9.0  9.0       9.0  9.0  8.5  9.0                      2.000                                                                             6.0  9.0  4.0  9.0 9.0            9.0  9.0  7.0  9.0                      1.000                                                                             4.0  5.0  1.0  9.0 9.0  8.0       8.5  9.0  7.0  9.0                       .500                                                                             5.7  7.0  3.0  9.0 8.0  8.5       8.3  9.0  7.5  9.0                 6y.sub.2                                                                           4.000                                                                             2.0  0.0  6.0  0.0 0.0  4.0       7.0  9.0  7.0  5.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       5.0  8.0  4.0  2.0                 6z.sub.2                                                                           4.000                                                                             7.0  5.0  7.0  5.0 5.0  9.0       9.0  9.0  6.0  9.0                       .500                                                                             2.0  0.0  0.0  0.0 0.0  7.0       8.0  9.0  4.0  6.0                 6b.sub.3                                                                           4.000         1.0  3.0 2.0  9.0       8.0  9.0  8.0  9.0                      2.000         1.0  3.0 1.0  6.0       7.0  9.0  8.0  9.0                      1.000         1.0  1.0      3.0       7.0  9.0  7.0  8.0                       .500              1.0      3.0       7.0  9.0  7.0  6.0                 6c.sub.3                                                                           4.000         1.0  1.0 2.0  7.0       9.0  9.0  7.0  9.0                      2.000              1.0      6.0       7.0  9.0  7.0  8.0                      1.000                       6.0       7.0  9.0  7.0  7.0                       .500                       6.0       6.0  9.0  7.0  4.0                 6d.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 1.0  2.0       5.0  9.0  7.0  5.0                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  3.0       5.0  9.0  5.0  2.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  3.0       5.0  8.0  7.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  5.0       5.0  8.0  7.0  3.0                 6e.sub.3                                                                           1.000                                                                             0.0  0.0  0.0  0.0 0.0  4.0       0.0  4.0  0.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       0.0  4.0  0.0  0.0                       .250                                                                             0.0  0.0  0.0  0.0 0.0  1.0       1.0  5.0  0.0  0.0                 6f.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  3.0       6.0  9.0  2.0  2.0                      2.000                                                                             0.0  0.0  0.0  0.0 0.0  2.0       4.0  9.0  0.0  1.5                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       4.0  9.0  0.0  0.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  4.5       2.0  8.0  0.0  0.0                 6h.sub.3                                                                           4.000                                                                             4.0  8.0  2.5  9.0 9.0  3.0       4.0  9.0  7.0  7.0                      2.000                                                                             6.0  6.0  4.0  9.0 9.0  9.0       8.0  9.0  8.0  9.0                      1.000                                                                             6.0  5.0  2.0  8.0 8.0  9.0       8.0  9.0  7.0  9.0                       .500                                                                             6.0  4.0  0.0  7.0 5.0  5.0       4.0  9.0  7.0  9.0                 6i.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  6.0       3.0  9.0       6.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0            0.0  7.0  0.0  0.0                 6j.sub.3                                                                           4.000                                                                             0.0  0.0  2.0  0.0 0.0  8.0       8.0  9.0  8.0  7.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  8.0       8.0  9.0  7.0  0.0                 6k.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  6.0  0.0  0.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  6.0  0.0  0.0                 6l.sub.3                                                                           2.000                                                                             0.0  0.0  1.0  0.0 0.0  4.0       2.0  4.0  6.0  5.0                      1.000                                                                             0.0  0.0  1.0  0.0 0.0  1.0       3.0  5.0  3.0  6.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  1.0       1.0  4.0  4.0  2.0                 6m.sub.3                                                                           2.000                                                                             0.0  2.0  1.0  0.0 0.0  9.0       9.0  9.0  7.0  9.0                      1.000                                                                             0.0  2.0  1.0  0.0 0.0  8.0       8.0       6.0  9.0                       .500                                                                             0.0  1.0  0.0  0.0 0.0  7.0       8.0  9.0  6.0  7.0                 6n.sub.3                                                                           4.000                                                                             0.0  3.0  9.0  0.0 2.0  8.0       8.0  9.0  8.0  9.0                      2.000                                                                             0.0  2.0  9.0  0.0 0.0  8.0       8.0  9.0  6.0  9.0                      1.000                                                                             0.0  1.0  5.0  0.0 0.0            8.0  9.0  6.0  9.0                       .500                                                                             0.0  0.0  1.0  0.0 0.0  5.0       8.0  6.0  5.0  8.0                 6o.sub.3                                                                           4.000                                                                             7.0  5.0  2.0  8.0 6.0  7.0       7.0  9.0  8.0  9.0                      2.000                                                                             5.0  3.0       7.0 6.0  6.0       5.0  9.0  7.0  9.0                      1.000                                                                             4.0  2.0       6.0 2.0  6.0       4.0  9.0  7.0  9.0                       .500                                                                             1.0  1.0       3.0 1.0  4.0       4.0  9.0  7.0  9.0                 6p.sub.3                                                                           4.000                                                                             0.0  0.0  6.0  0.0 0.0  4.0       8.0  8.0       8.0                      2.000                                                                             0.0  0.0  2.0  0.0 0.0  0.0       7.0  8.0  6.0  6.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       7.0  7.0  4.0  5.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       6.0  7.0  1.0  4.0                 6q.sub.3                                                                           4.000                                                                             1.0  0.0  0.0  0.0 0.0  2.0       2.0       0.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       2.0  9.0  0.0  1.0                 6r.sub.3                                                                           4.000                                                                             1.0  0.0  0.0  3.0 0.0  0.0       0.0  2.0  0.0  2.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  2.0  0.0                      6s.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  2.0       0.0  6.0  0.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0  6.0  0.0  1.0                 6t.sub.3                                                                           4.000                                                                             0.0       0.0  0.0 0.0  0.0       0.0  5.0  0.0  3.0                 __________________________________________________________________________    Com-                                                                          pound                                                                         of        BARNY                                                                              FOXTA P NUT                                                                              WILD QUACK                                                                              FLD B                                                                              MRNGL WILD RAG  VELVE                Example                                                                            RATE ARDGR                                                                              IL SP SEDGE                                                                              OATS GRASS                                                                              INDWD                                                                              RY SP MUSTD                                                                              WEED TLEAF                __________________________________________________________________________    10d  1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        1.0  0.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        1.0  0.0                  10e  1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        2.0  0.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        5.0  0.0                  10f  1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        0.0  2.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        0.0  0.0                  10g  1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        0.0  1.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        0.0  1.0                  10h  4.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  0.0        6.0  6.0                       2.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  0.0        4.0  8.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  0.0        3.0  3.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        2.0  2.0                  10i  4.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        7.0  2.0                       2.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        7.0  2.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        8.0  2.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        1.0  0.0                  10k  4.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  2.0        8.0  9.0                       2.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  1.0        7.0  9.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        7.0  8.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        4.0  9.0                  10l  4.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  0.0        3.0  1.0                       2.000                                                                              0.0  0.0   0.0  0.0  0.0  3.0  0.0        2.0  0.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        1.0  0.0                  10m  4.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        6.0  2.0                       2.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        5.0  1.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        1.0  0.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0        2.0  0.0                  10n  4.000                                                                              6.0  9.0   7.0  3.0  4.0  2.0  6.0   9.0  9.0  9.0                        .500                                                                              0.0  5.0   4.0  0.0  0.0  1.0  4.0   9.0  6.0  9.0                  10o  4.000                                                                              5.0  5.0   5.0  2.0  5.0  2.0  5.0   9.0  8.0  9.0                        .500                                                                              2.0  0.0   0.0  0.0  0.0  1.0  1.0   7.0  4.0  7.0                  10p  4.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0   7.0  0.0  1.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0   5.0  0.0  0.0                  11a  4.000                                                                              2.0  1.0   0.0  0.0  1.0  5.0  4.0   9.0  7.0                             .500                                                                              0.0  0.0   0.0  0.0  0.0  1.0  3.0   7.0  3.0  9.0                  11b  4.000                                                                              0.0  0.0   0.0  0.0  0.0  3.0  4.0   7.0  5.0  3.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0   0.0  3.0  1.0                  11c  4.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  2.0   7.0  4.0                             .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0   2.0  0.0  2.0                  11d  4.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0   3.0  0.0  0.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0        6.0       0.0                  11e  4.000                                                                              0.0  0.0   0.0  0.0  0.0  2.0  0.0   5.0                                  .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0   1.0  2.0  5.0                  11f  4.000                                                                              0.0  5.0   0.0  0.0  0.0  3.0  2.0   9.0       9.0                        .500                                                                              0.0  1.0   0.0  0.0  0.0  1.0  1.0   6.0  6.0  5.0                  11g  4.000                                                                              0.0  5.0   0.0  0.0  0.0  4.0  3.0   7.0  7.0  9.0                        .500                                                                              0.0  1.0   0.0  0.0  0.0  2.0  0.0   2.0  3.0  8.0                  11h  4.000                                                                              0.0  0.0   0.0  0.0  0.0  7.0  7.0   6.0  6.0  4.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  1.0  2.0   2.0       1.0                  11i  4.000                                                                              0.0  0.0   0.0  0.0  0.0  3.0  2.0   6.0       2.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  1.0  1.0   4.0       1.0                  18a  4.000                                                                              0.0  1.0   1.0  1.0  2.0  2.0  5.0   9.0  4.0  8.0                       2.000                                                                              1.0  0.0   0.0  0.0  1.0  2.0  4.0   9.0  4.0  6.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  2.0  1.0   9.0  3.0  2.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  1.0  1.0   9.0  0.0  1.0                  19a  4.000                                                                              2.0  2.0   3.0  0.0  1.0  9.0  9.0   9.0  8.0  9.0                       2.000                                                                              0.0  1.0   4.0  0.0  0.0  9.0  8.0   9.0  7.0  9.0                       1.000                                                                              0.0  1.0   1.0  0.0  0.0  9.0  8.0   9.0  7.0  8.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  5.0  6.5   9.0  7.0  7.0                  20a  4.000                                                                              0.0  2.0   7.0  0.0  5.0  5.0  1.0        9.0  9.0                       2.000                                                                              0.0  2.0   3.0  0.0  2.0  2.0  0.0        7.0  9.0                       1.000                                                                              0.0  0.0   0.0  0.0  1.0  2.0  0.0        7.0  9.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  1.0  0.0        7.0  9.0                  21a  4.000                                                                              0.0  1.0   8.0  0.0  4.0  6.0  1.0        9.0  9.0                       2.000                                                                              0.0  0.0   1.0  0.0  1.0  2.0  0.0        6.0  9.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  2.0  0.0        6.0  9.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  1.0  0.0        6.0  9.0                  21b  4.000                                                                              8.0  9.0   6.0  9.0  9.0  9.0  9.0   9.0  9.0  9.0                       2.000                                                                              8.0  8.0   6.0  9.0  7.0  9.0  9.0   9.0  9.0  9.0                       1.000                                                                              7.0  9.0   5.0  8.0  6.0  9.0  9.0   9.0  9.0  9.0                        .500                                                                              4.0  6.0   0.0  7.0  2.0  6.0  9.0   9.0  9.0  9.0                  21c  4.000                                                                              0.0  0.0   0.0  0.0  0.0  4.0  7.0   8.0  0.0  2.0                       2.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  5.0   8.0  0.0  1.0                       1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  6.0   9.0  0.0  0.0                        .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  5.0   9.0  0.0  0.0                  __________________________________________________________________________

EXAMPLE 23

Preemergence herbicidal evaluation of test compounds

The preemergence herbicidal activity of the compounds of the presentinvention is exemplified by the following tests in which the seeds of avariety of monocotyledonous and dicotyledonous plants are separatelymixed with potting soil and planted on top of approximately one inch ofsoil in separate pint cups. After planting, the cups are sprayed withthe selected aqueous acetone solution containing test compound insufficient quantity to provide the equivalent of about 0.032 kg to 8 kgper hectare of test compound per cup. The treated cups are then placedon greenhouse benches, watered and cared for in accordance withconventional greenhouse procedures. From four to five weeks aftertreatment, the test are terminated and each cup is examined and ratedaccording to the rating system set forth above. The herbicidalproficiency of the active ingredients of the present invention isevident from the test results which are recorded in Table VII below.Where more than one test is involved for a given compound, the data areaveraged.

                                      TABLE VII                                   __________________________________________________________________________    PRE-EMERGENCE TESTS - RATES IN KG/HA                                          __________________________________________________________________________    Com-                                                                          pound of BARNY                                                                              FOXTA                                                                              P NUT                                                                              WILD                                                                              QUACK                                                                              FLD B                                                                              MATRI                                                                              MRNGL                                                                              WILD RAGWE                                                                              VELVE               Example                                                                            RATE                                                                              ARDGR                                                                              IL SP                                                                              SEDGE                                                                              OATS                                                                              GRASS                                                                              INDWD                                                                              C SPP                                                                              RY SP                                                                              MUSTD                                                                              ED   TLEAF               __________________________________________________________________________    5a   2.000         9.0      4.0       9.0  7.0  9.0  8.0  9.0                      1.500         2.0      4.0       9.0  6.0  8.0  7.0  9.0                      1.000                                                                             0.0  1.0  4.3  1.0 3.0  8.0  8.0  5.0  6.0  7.5  8.5                       .750         4.0      1.0       8.0  3.0  7.0  5.0  8.0                       .500                                                                             0.0  1.0  2.0  0.0 2.5  6.0  8.0  3.5  5.0  4.0  7.0                 5b   4.000                                                                             8.0  9.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             8.0  9.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             5.0  6.0  9.0  5.0 9.0  9.0       9.0  9.0  9.0  9.0                       .500                                                                             4.0  9.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                 5c   4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       5.0  0.0  6.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       4.0  0.0  4.0  1.0                 5d   4.000                                                                             0.0  0.0  3.0  0.0 2.0  7.0       8.0  7.0  2.0  5.0                      2.000                                                                             0.0  0.0  2.0  0.0 1.0  5.0       6.0  9.0  4.0  1.0                      1.000                                                                             0.0  0.0  5.0  0.0 2.0  4.0       4.0  3.0  0.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  2.0       2.0  0.0  0.0  0.0                 5e   4.000                                                                             8.5  9.0  9.0  8.0 9.0  9.0       8.5  9.0  8.5  8.5                      2.000                                                                             8.0  9.0  9.0  7.5 9.9  9.0       7.0  9.0  9.0  9.0                      1.000                                                                             8.5  7.0  9.0  7.0 9.0  9.0       9.0  9.0  9.0  9.0                       .500                                                                             5.5  6.0  9.0  6.6 9.0  8.0       8.0  9.0  9.0  8.0                 5f   4.000                                                                             8.0  7.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             3.0  3.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             3.0  7.0  9.0  2.0 6.0  9.0       9.0  9.0  9.0  9.0                       .500                                                                             0.0  5.0  9.0  0.0 5.0  9.0       9.0  9.0  7.0  9.0                 5g   4.000                                                                             1.0  0.0  8.0  4.0 1.0  8.0       9.0  9.0  9.0  9.0                      2.000                                                                             2.0  2.0  6.0  2.0 0.0  6.0       8.0  8.0  7.0  8.0                      1.000                                                                             1.0  1.0  6.0  2.0 1.0  5.0       8.0  9.0  6.0  9.0                       .500                                                                             0.0  0.0  2.0  0.0 0.0  2.0       8.0  5.0  4.0  4.0                 5h   1.000                                                                             6.0  6.0  9.0  4.0 4.0  9.0       9.0  9.0  9.0  9.0                       .500                                                                             3.0  5.0  9.0  0.0 4.0  9.0       9.0  9.0  9.0  9.0                 6a.sub.1                                                                           4.000                                                                             3.6  4.6  9.0  3.4 8.6  9.0  9.0  8.1  8.6  8.2  8.7                      2.000                                                                             2.9  3.6  8.7  2.4 7.4  8.8  8.3  7.6  7.9  7.2  8.4                      1.500         4.0      4.0       9.0  7.0  8.0  4.0  9.0                      1.000                                                                             1.0  2.7  7.3  1.1 6.1  8.3  7.5  6.3  7.7  7.2  8.4                       .750         7.0  0.0 1.0       8.0  5.5  7.0  6.0  8.5                       .600                            9.0  8.0  9.0  8.0  9.0                       .500                                                                             0.5  1.4  7.1  1.0 4.7  8.0  7.3  5.2  7.3  6.0  7.7                 6b.sub.1                                                                           4.000                                                                             0.0  0.0  5.0  0.0 1.0  3.0       4.0       6.0  8.0                      2.000                                                                             0.0  0.0  4.0  0.0 0.0  2.0       3.0       5.0  8.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0       3.0  4.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       0.0       2.0  4.0                 6c.sub.1                                                                           4.000                                                                             1.5  1.5  1.0  3.5 4.5  2.0       5.0  5.0  5.0  2.5                      2.000                                                                             0.5  0.0  0.0  0.0 0.0  1.0       2.5  3.0  4.5  1.5                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.5  2.0  2.0  1.5                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0  0.0  0.0  0.5                 5d.sub.1                                                                           4,000                                                                             3.0       9.0  0.0 3.0  9.0       8.0  8.0  8.0  6.0                      1.000                                                                             0.0  0.0  5.0  2.0 0.0  9.0       5.0       5.0  5.0                       .500                                                                             0.0  0.0  4.0  0.0 0.0  5.0       4.0            5.0                 6e.sub.1                                                                           1.000                                                                             0.0  0.0  2.0  0.0 0.0  1.0       3.0       0.0  2.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0       0.0  1.0                 6f.sub.1                                                                           4.000                                                                             1.5  1.5  1.0  3.5 4.5  2.0       5.0  5.0  5.0  2.5                      2.000                                                                             0.5  0.0  0.0  0.0 0.0  1.0       2.5  3.0  4.5  1.5                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.5  2.0  2.0  1.5                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0  0.0  0.0  0.5                 6g.sub.1                                                                           4.000                                                                             2.0  2.0  9.0  8.0 9.0  7.0       9.0       9.0  9.0                      2.000                                                                             6.0  2.0  9.0  7.0 9.0  9.0       9.0       9.0  9.0                      1.000                                                                             1.0  0.0  2.0  4.0 2.0  3.0       9.0       9.0  8.0                       .500                                                                             3.0  2.0  6.0  5.0 8.0  7.0       9.0       7.0  8.0                 6h.sub.1                                                                           4.000                                                                             2.0  2.0  9.0  8.0 9.0  7.0       9.0       9.0  9.0                      2.000                                                                             6.0  2.0  9.0  7.0 9.0  9.0       9.0       9.0  9.0                      1.000                                                                             1.0  0.0  2.0  4.0 2.0  3.0       9.0       9.0  8.0                       .500                                                                             3.0  2.0  6.0  5.0 8.0  7.0       9.0       7.0  8.0                 6i.sub.1                                                                           4.000                                                                             8.0  4.0  9.0  6.0 9.0  9.0       7.0  9.0  6.0  9.0                      2.000                                                                             6.0  7.0  6.0  3.0 9.0  8.0       7.0  9.0  4.0  9.0                      1.000                                                                             6.0  6.0  9.0  5.0 9.0  9.0       4.0  9.0  6.0  9.0                       .500                                                                             2.0  3.0  9.0  3.0 9.0  5.0       4.0  9.0  4.0  9.0                 6j.sub.1                                                                           4.000                                                                             6.1  8.1  9.0  7.4 9.0  9.0       9.0  9.0  8.3  9.0                      3.000                                                                             8.0  7.0  9.0  7.0 9.0  9.0       9.0  9.0  7.0  9.0                      2.000                                                                             7.0  7.3  9.0  7.4 8.9  9.0  9.0  8.6  8.9  8.3  8.8                      1.000                                                                             4.9  6.7  9.0  6.9 9.0  8.8  8.8  7.8  8.9  8.4  8.6                       .800                                                                             5.0  6.0  9.0  5.0 9.0  9.0       8.0  9.0  5.0  8.0                       .500                                                                             3.6  5.1  8.7  5.5 8.7  8.1  8.8  7.1  8.8  7.6  8.1                 6k.sub.1                                                                           4.000                                                                             0.0  3.0  4.0  0.0 2.0  1.0       3.0  3.0  2.0  1.0                       .500                                                                             0.0  0.0  3.0  0.0 0.0  0.0       2.0  3.0  2.0  1.0                 6l.sub.1                                                                           4.000                                                                             0.0  0.0  4.0  0.0 4.0  1.0       5.0  7.0  3.0  8.0                       .500                                                                             0.0  0.0  2.0  0.0 3.0  1.0       2.0  3.0  2.0  7.0                 6m.sub.1                                                                           4.000                                                                             5.0  6.0  9.0  7.0 9.0  9.0       9.0  9.0  7.0  9.0                      2.000                                                                             9.0  9.0  9.0  8.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             6.7  8.5  9.0  6.5 9.0  9.0       8.3  9.0  8.0  9.0                       .500                                                                             4.0  5.5  8.6  5.8 9.0  7.5       8.4  8.5  7.3  8.5                      .250                                                                              4.3  6.3  7.8  6.0 9.0  8.3       7.5  9.0  4.7  8.7                 6n.sub.1                                                                           4.000                                                                             0.0  4.0  9.0  4.0 7.0  9.0       8.0  9.0  8.0  9.0                      3.000                                                                             0.0  3.0  9.0  3.0 9.0  9.0       8.0  9.0  9.0  9.0                      2.000                                                                             0.0  7.0  9.0  2.0 9.0  9.0       8.0  9.0  9.0  9.0                      1.000                                                                             0.0  2.0  9.0  1.0 7.0  9.0       8.0  8.0  8.0  9.0                       .800                                                                             0.0  2.0  9.0  2.0 9.0  9.0       8.0  8.0  9.0  9.0                       .500                                                                             0.0  0.0  8.0  1.0 6.0  9.0       8.0  9.0  9.0  9.0                 6o.sub.1                                                                           4.000                                                                             3.0  2.0  7.0  0.0 8.0  9.0       9.0  9.0  8.0  6.0                       .500                                                                             0.0  0.0  1.0  0.0 8.0  3.0       4.0  7.0  2.0  2.0                 6q.sub.1                                                                           4.000                                                                             0.5  0.0  9.0  0.5 4.5  9.0       9.0  9.0  8.0  9.0                      2.000                                                                             1.0  0.0  8.0  0.0 4.0  9.0       9.0  9.0  5.0  9.0                      1.000                                                                             0.0  0.0  8.0  0.0 3.0  9.0       9.0  9.0  4.0  7.0                       .500                                                                             0.0  0.0  5.0  0.0 1.5  5.5       8.0  9.0  3.0  8.0                 6r.sub.1                                                                           4.000                                                                             8.0  9.0  9.0  8.0 9.0  9.0       9.0  9.0  8.0  9.0                      1.000                                                                             2.0  2.0  9.0  4.0 9.0  3.0       6.0  9.0  9.0  7.0                       .500                                                                             2.0  1.5  8.5  3.5 9.0  4.0       5.5  9.0  4.0  7.5                 6s.sub.1                                                                           4.000                                                                             5.0  5.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             1.0  1.0  7.0  1.0 9.0  9.0       9.0  9.0  4.0  9.0                       .500                                                                             3.5  1.0  9.0  3.0 8.0  9.0       9.0  9.0  6.0  9.0                 6t.sub.1                                                                           4.000                                                                             5.0  2.5  9.0  7.5 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             3.0  6.0  9.0  8.0 9.0  9.0       9.0  9.0  9.0  7.0                      1.000                                                                             0.0  0.0  8.0  6.0 9.0  9.0       9.0  9.0  8.0  6.0                       .500                                                                             1.0  0.5  4.5  5.0 8.0  7.0       9.0  8.5  5.0  5.5                 6u.sub.1                                                                           4.000                                                                             1.0  0.0  9.0  2.0 5.0  9.0       9.0  9.0  9.0  6.0                      1.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       7.0  9.0  2.0  1.0                       .500                                                                             0.5  0.0  4.5  1.0 1.5  1.5       4.5  7.0  2.5  3.5                 6v.sub.1                                                                           4.000                                                                             0.0  1.0  0.0  1.0 1.0  2.0       6.0  3.0  0.0  2.0                       .500                                                                             0.0  0.0  0.0  1.0 1.0  4.0       6.0  1.0  2.0  1.0                 6w.sub.1                                                                           4.000                                                                             0.5  5.0  9.0  0.5 8.0  9.0       9.0  8.5  6.5  9.0                      2.000                                                                             0.0  0.0  9.0  0.0 5.0  9.0       9.0  9.0  5.0  8.0                      1.000                                                                             0.0  0.0  6.0  0.0 1.0  9.0       8.0  7.0  2.0  5.0                       .500                                                                             0.0  0.0  5.5  0.5 2.5  9.0       8.5  7.0  3.0  5.0                 6x.sub.1                                                                           4.000                                                                             0.0  0.0  6.0  1.0 9.0  9.0       9.0  6.0  2.0  4.0                       .500                                                                             0.0  0.0  5.0  1.0 2.0  6.0       4.0  4.0  2.0  1.0                 6y.sub.1                                                                           4.000                                                                             2.0  1.0  9.0  6.0 9.0  8.0       9.0  9.0  9.0  8.0                       .500                                                                             6.0  0.0  5.0  1.0 7.0  8.0       6.0  9.0  4.0  7.0                 6z.sub.1                                                                           4.000                                                                             0.5  0.0  1.5  0.5 0.5  0.5       2.5  1.0  1.0  2.0                       .500                                                                             0.0  0.0  1.0  0.0 0.0  0.0       3.0  1.0  1.5  2.0                 6a.sub.2                                                                           4.000                                                                             0.0  2.0  3.0  0.0 4.0  9.0       9.0  9.0  1.0  8.0                       .500                                                                             0.0  1.0  9.0  0.0 1.0  9.0       7.0  9.0  2.0  8.0                 6b.sub.2                                                                           4.000                                                                             0.0  2.0  0.0  0.0 0.0  0.0       5.0  6.0  2.0  6.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       5.0  9.0  1.0  6.0                 6c.sub.2                                                                           4.000                                                                             5.0  5.0  9.0  7.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             3.0  5.0  9.0  4.0 9.0  9.0       5.0  9.0  7.0  9.0                       .500                                                                             2.0  2.0  8.0  5.0 9.0  9.0       6.0  9.0  7.0  8.5                 6d.sub.2                                                                           4.000                                                                             0.0  1.0  6.0  0.0 0.0  3.0       1.0  8.0  0.0  7.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  2.0       0.0  1.0  0.0  1.0                 6e.sub.2                                                                           4.000                                                                             0.0  0.0  6.0  1.0 7.0  1.0       7.0  8.0  7.0  3.0                       .500                                                                             0.0  0.0  2.0  1.0 4.0  1.0       5.0  2.0  2.0  2.0                 6f.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 1.0  1.0       4.0  7.0  2.0  3.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       2.0  6.0  2.0  1.0                 6g.sub.2                                                                           4.000                                                                             0.0  1.0  5.0  2.0 4.0  2.0       5.0  6.0  2.0  5.0                       .500                                                                             0.0  0.0  1.0  1.0 2.0  3.0       2.0  5.0  2.0  4.0                 6h.sub.2                                                                           4.000                                                                             1.0  0.0  6.0  0.0 0.0  7.0       6.0  5.0  2.0  5.0                       .500                                                                             0.0  0.0  4.0  0.0 0.0  4.0       5.0  4.0  2.0  3.0                 6i.sub.2                                                                           4.000                                                                             1.0  0.0  2.0  2.0 4.0  6.0       5.0  7.0  1.0  4.0                       .500                                                                             3.0  0.0  3.0  1.0 0.0  3.0       3.0  6.0  0.0  1.0                 6j.sub.2                                                                           4.000                                                                             3.0  2.0  7.0  3.0 9.0  9.0       8.0  8.0  5.0  8.0                       .500                                                                             0.0  0.0  3.0  0.0 4.0  4.0       5.0  5.0  0.0  5.0                 6k.sub.2                                                                           4.000                                                                             9.0  9.0  9.0  9.0 9.0  9.0       9.0  9.0  9.0  9.0                      3.000                                                                             9.0  9.0  9.0  9.0 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             9.0  9.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             5.5  9.0  9.0  6.0 9.0  9.0       8.0  9.0  8.0  9.0                       .800                                                                             9.0  9.0  9.0  6.0 9.0  9.0       9.0  9.0  7.0  9.0                       .500                                                                             4.3  7.5  9.0  6.5 9.0  9.0       8.0  9.0  8.0  9.0                 6l.sub.2                                                                           4.000                                                                             7.0  7.0  9.0  5.0 9.0  8.0       9.0  9.0  7.0  9.0                       .500                                                                             4.0  4.0  9.0  1.0 9.0  8.0       4.0  9.0  2.0  5.0                 6m.sub.2                                                                           4.000                                                                             3.0  2.0  8.0  1.0 7.0  8.0       6.0  7.0  6.0  7.0                       .500                                                                             0.0  0.0  3.0  0.0 9.0  4.0       5.0  6.0  4.0  5.0                 6n.sub.2                                                                           4.000                                                                             5.0  5.0  9.0  6.0 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             2.0  4.0  9.0  0.5 9.0  9.0  9.0  8.5  9.0  6.0  9.0                      1.000                                                                             3.0  4.0  9.0  1.0 6.3  9.0  9.0  8.5  8.8  7.7  8.5                       .750              0.0 0.0       8.0  6.0  5.0       7.0                       .600                            9.0  9.0  9.0  8.0  9.0                       .500                                                                             1.3  2.0  7.7  0.3 3.3  9.0  8.0  8.3  8.0  5.0  7.5                 6o.sub.2                                                                           4.000                                                                             6.0  6.0  9.0  4.0 9.0  9.0       5.0  5.0  0.0  7.0                       .500                                                                             0.0  1.0  2.0  0.0 0.0  2.0       3.0  6.0  0.0  7.0                 6p.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  1.0       2.0  0.0  0.0  0.0                 6q.sub.2                                                                           4.000                                                                             0.0  0.0  1.0  0.0 1.0  3.0       6.0  0.0  0.0  2.0                       .500                                                                             0.0  0.0  2.0  0.0 0.0  0.0       0.0  0.0  0.0  0.0                 6r.sub.2                                                                           4.000                                                                             2.0  0.0  7.0  2.0 4.0  6.0       6.0  6.0  4.0  5.0                       .600                            0.0  0.0  0.0  1.0  0.0                       .500                                                                             0.0  0.0  5.0  0.0 2.0  2.0       6.0  0.0  5.0  2.0                 6s.sub.2                                                                           4.000                                                                             0.0  0.0  4.0  0.0 1.0  2.0       0.0  0.0  0.0  0.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  2.0       0.0  0.0  0.0  0.0                 6t.sub.2                                                                           4.000                                                                             7.5  6.0  9.0  6.5 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             7.5  5.5  9.0  4.5 9.0  9.0       9.0  9.0  8.5  9.0                      1.000                                                                             3.3  4.5  9.0  4.5 7.5  9.0       8.7  9.0  8.0  8.5                       .500                                                                             2.7  3.0  7.3  3.5 6.0  9.0       8.7  9.0  8.0  7.0                 6u.sub.2                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       5.0  8.0  0.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       1.0  9.0  0.0  1.0                 6v.sub.2                                                                           4.000                                                                             0.0  0.0  8.0  0.0 3.0  1.0       6.0  9.0  4.0  9.0                       .500                                                                             0.0  0.0  7.0  0.0 0.0  0.0       0.0  2.0  0.0  2.0                 6w.sub.2                                                                           4.000                                                                             6.5  7.0  9.0  7.0 8.0  9.0       8.0  9.0  8.5  9.0                      2.000                                                                             7.0  9.0  9.0  7.0 9.0  9.0       8.0  9.0  9.0  9.0                      1.000                                                                             7.0  6.0  9.0  6.0 9.0  8.0       8.0  9.0  8.0  8.0                       .500                                                                             3.5  1.5  8.0  4.5 9.0  9.0       7.0  9.0  5.5  8.5                 6x.sub.2                                                                           4.000                                                                             9.0  9.0  9.0  7.5 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             9.0  9.0  9.0  8.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             5.0  9.0  8.5  7.0 9.0  9.0       8.5  9.0  9.0  9.0                 6y.sub.2                                                                           4.000                                                                             1.0  4.0  3.0  4.0 2.0  4.0       8.0  9.0  6.0  8.0                       .500                                                                             0.0  1.0  3.0  0.0 4.0  9.0       8.0  9.0  8.0  7.0                 6z.sub.2                                                                           4.000                                                                             4.0  7.0  9.0  7.0 9.0  9.0       9.0  9.0  9.0  9.0                       .500                                                                             0.0  1.0  0.0  0.0 7.0  3.0       8.0  7.0  1.0  7.0                 6a.sub.3                                                                           2.000                                                                             0.0  0.0  3.0  1.0 1.0  0.0       3.0  3.0  2.0  2.0                      1.000                                                                             0.0  0.0  1.0  0.0 0.0  0.0       7.0  0.0  6.0  0.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       7.0  5.0  0.0  5.0                 6c.sub.3                                                                           4.000         1.0  1.0 2.0  7.0       9.0  9.0  7.0  9.0                      2.000              1.0      6.0       7.0  9.0  7.0  8.0                      1.000                       6.0       7.0  9.0  7.0  7.0                       .500                       6.0       6.0  9.0  7.0  4.0                 6d.sub.3                                                                           4.000                                                                             1.0  0.0  9.0  2.0 9.0  9.0       8.0  6.0  8.0  3.0                      2.000                                                                             0.0  0.0  9.0  0.0 9.0  9.0       7.0  6.0  7.0  1.0                      1.000                                                                             0.0  0.0  0.0  0.0 9.0  9.0       7.0  7.0  0.0  2.0                       .500                                                                             0.0  0.0  0.0  0.0 9.0  9.0       6.0  9.0  0.0  1.0                 6e.sub.3                                                                           2.000                                                                             2.0  0.0  2.0  1.0 0.0  6.0       6.0       3.0  2.0                      1.000                                                                             0.0  0.0  1.0  0.0 0.0  0.0       3.0       1.0  3.0                       .500                                                                             0.0  0.0  9.0  0.0 0.0            5.0       0.0  3.0                 6f.sub.3                                                                           4.000                                                                             0.0  0.0  8.0  1.0 5.0  8.0       8.5  6.0  7.5  4.5                      2.000                                                                             0.0  0.0  3.5  0.0 1.5  5.5       8.5  6.0  4.5  1.0                      1.000                                                                             0.0  0.0  2.0  0.0 1.5  5.0       7.0  6.0  2.0  3.0                       .500                                                                             0.0  0.0  1.5  0.0 0.5  1.0       3.5  1.0  0.0  0.0                 6g.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  2.0       3.0  0.0  3.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0            5.0  0.0  0.0                      6h.sub.3                                                                           4.000                                                                             8.0  7.0  9.0  8.5 9.0  9.0       8.5  8.0  8.5  8.5                      2.000                                                                             5.0  6.0  9.0  6.5 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             5.5  6.0  9.0  7.5 9.0  9.0       9.0  9.0  9.0  9.0                       .500                                                                             5.0  4.0  9.0  6.5 9.0  7.0       8.0  9.0  9.0  8.0                 6i.sub.3                                                                           4.000                                                                             0.0  0.0  1.0  0.0 1.0  1.0       7.0  7.0  3.0  4.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       7.0  3.0  0.0  1.0                 6j.sub.3                                                                           4.000                                                                             0.0  0.0  9.0  0.0 5.0  9.0       9.0  9.0  9.0  7.0                       .500                                                                             0.0  0.0  9.0  0.0 0.0  9.0       8.0  9.0  9.0  2.0                 6l.sub.3                                                                           2.000                                                                             0.0  0.0  4.0  0.0 0.0  9.0       6.0  8.0  6.0  8.0                      1.000                                                                             0.0  0.0  3.0  0.0 0.0  0.0       5.0  6.0  4.0  6.0                       .500                                                                             0.0  0.0  1.0  0.0 0.0  1.0       5.0  5.0  3.0  4.0                 6m.sub.3                                                                           2.000                                                                             5.0  9.0  9.0  4.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             3.0  2.0  9.0  2.0 5.0  9.0       9.0  9.0  8.0  9.0                       .600                            8.0  9.0  9.0  7.0  9.0                       .500                                                                             0.0  0.0  9.0  0.0 2.0  9.0       9.0  9.0  8.0  9.0                 6n.sub.3                                                                           4.000                                                                             4.0  7.0  9.0  4.0 9.0  9.0       9.0  9.0  9.0  9.0                      2.000                                                                             3.0  5.0  9.0  4.0 9.0  9.0       9.0  9.0  9.0  9.0                      1.000                                                                             1.0  3.0  9.0  1.0 9.0  9.0       9.0  9.0  9.0  9.0                       .600                            9.0  9.0  9.0  7.0  9.0                       .500                                                                             0.0  0.0  9.0  0.0 9.0  9.0       9.0  8.0  7.0  9.0                 6p.sub.3                                                                           4.000                                                                             5.0  4.0  8.0  6.0 8.0  9.0  9.0  9.0  8.0  9.0                           2.000                                                                             3.0  1.0  9.0  1.0 8.0  8.0       9.0  9.0  7.0  9.0                      1.000                                                                             1.0  0.0  7.0  5.0 2.0  5.0       9.0  9.0  9.0  9.0                       .500                                                                             4.0  0.0  5.0  5.0 2.0  4.0       9.0  9.0  3.0  8.0                 6q.sub.3                                                                           4.000                                                                             0.0  0.0  2.0  0.0 1.0  0.0       3.0  2.0  0.0  8.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  6.0       7.0  2.0  0.0  1.0                 6r.sub.3                                                                           4.000                                                                             0.0  0.0  1.0  0.0 2.0  0.0       3.0  1.0  0.0  1.0                       .500                                                                             0.0  0.0  0.0  0.0 0.0  0.0       5.0  0.0  0.0  0.0                 6s.sub.3                                                                           4.000                                                                             0.0  0.0  0.0  0.0 0.0  0.0       5.0  1.0  0.0  1.0                 __________________________________________________________________________    Compound of BARNY                                                                              FOXTA P NUT                                                                              WILD QUACK                                                                              FLD B                                                                              MRNGL                                                                              WILD RAGWE                                                                              VELVE               Example                                                                              RATE ARDGR                                                                              IL SP SEDGE                                                                              OATS GRASS                                                                              INDWD                                                                              RY SP                                                                              MUSTD                                                                              ED   TLEAF               __________________________________________________________________________    10b    4.000                                                                              0.0  0.0   4.0  0.0  0.0  3.0  6.0       8.0  9.0                        2.000                                                                              1.0  0.0   4.0  1.0  1.0  3.0  6.0       6.0  8.0                        1.000                                                                              0.0  0.0   1.0  0.0  0.0  1.0  3.0       6.0  7.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0       5.0  6.0                 10c    4.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  2.0       1.0  4.0                        2.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  2.0       0.0  3.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  2.0       0.0  0.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0       0.0  0.0                 10d    4.000                                                                              0.0  1.0   0.0  0.0  0.0  1.0  6.0       6.0  7.0                        2.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  2.0       4.0  4.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0       2.0  3.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0       1.0  1.0                 10e    4.000                                                                              0.0  0.0   0.0  0.0  4.0  9.0  8.0       8.0  8.0                        2.000                                                                              0.0  0.0   0.0  0.0  2.0  2.0  7.0       4.0  7.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  1.0       1.0  2.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0       0.0  4.0                 10f    4.000                                                                              0.0  0.0   0.0  0.0  4.0  5.0  0.0       6.0  6.0                        2.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0       3.0  7.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0       3.0  0.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0       2.0  0.0                 10g    4.000                                                                              0.0  2.0   0.0  0.0  2.0  2.0  5.0       6.0  8.0                        2.000                                                                              0.0  0.0   0.0  0.0  2.0  0.0  1.0       5.0  7.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0       2.0  6.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0       0.0  5.0                 10h    4.000                                                                              3.0  3.0   6.0  3.0  6.0  6.0  6.0  9.0  9.0  9.0                        2.000                                                                              2.0  3.0   2.0  2.0  4.0  7.0  7.0  8.0  8.0  8.0                        1.000                                                                              1.0  1.0   0.0  1.0  2.0  1.0  4.0  6.0  6.0  7.0                         .500                                                                              0.0  0.0   0.0  0.0  1.0  0.0  2.0  6.0  6.0  7.0                 10i    4.000                                                                              4.0  6.0   3.0  1.0  7.0  7.0  7.0  7.0  7.0  8.0                        2.000                                                                              4.0  5.0   3.0  1.0  7.0  7.0  6.0  8.0  7.0  8.0                        1.000                                                                              2.0  4.0   2.0  1.0  7.0  5.0  5.0  7.0  7.0  7.0                         .500                                                                              1.0  3.0   1.0  1.0  4.0  5.0  3.0  7.0  6.0  6.0                 10j    2.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0  8.0  7.0  7.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0  2.0  6.0  4.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0  3.0  7.0  5.0                 10k    4.000                                                                              5.0  9.0   6.0  2.0  9.0  9.0  7.0  9.0  9.0  9.0                        2.000                                                                              5.0  6.0   6.0  1.0  9.0  9.0  6.0  9.0  9.0  9.0                        1.000                                                                              4.0  4.0   6.0  1.0  5.0  5.0  5.0  9.0  9.0  9.0                         .500                                                                              4.0  3.0   5.0  0.0  6.0  5.0  6.0  9.0  9.0  8.0                 10l    4.000                                                                              0.0  1.0   0.0  0.0  0.0  0.0  0.0  0.0  0.0  0.0                 10m    4.000                                                                              0.0  0.0   0.0  0.0  0.0  7.0  3.0  4.0  6.0  6.0                        2.000                                                                              0.0  0.0   0.0  0.0  0.0  6.0  5.0  4.0  5.0  5.0                        1.000                                                                              0.0  0.0   0.0  0.0  0.0  0.0  1.0  1.0  2.0  3.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0       0.0  0.0  2.0  2.0                 10n    4.000                                                                              5.0  6.0   9.0  6.0  9.0  9.0  7.0  9.0  9.0  9.0                         .500                                                                              0.0  8.0   9.0  1.0  9.0  9.0  4.0  9.0  9.0  7.0                 10o    4.000                                                                              0.0  5.0   5.0  2.0  8.0  8.0  6.0  6.0  9.0  9.0                         .500                                                                              0.0  0.0   8.0  0.0  6.0  0.0  5.0  5.0  0.0  6.0                 10p    4.000                                                                              0.0  0.0   0.0  0.0  0.0  1.0  1.0  7.0  0.0  5.0                         .500                                                                              0.0  0.0   0.0  0.0  2.0  0.0  0.0  2.0  0.0  1.0                 11a    4.000                                                                              1.0  0.0   6.0  3.0  9.0  8.0  5.0  9.0  7.0  8.0                         .500                                                                              0.0  0.0   3.0  1.0  6.0  2.0  2.0  9.0  1.0  7.0                 11b    4.000                                                                              1.0  2.0   6.0  3.0  6.0  9.0  7.0  7.0  7.0  7.0                         .500                                                                              0.0  0.0   2.0  1.0  4.0  8.0  6.0  4.0  2.0  1.0                 11c    4.000                                                                              1.0  1.0   3.0  1.0  9.0  8.0  4.0  8.0  3.0  7.0                         .500                                                                              0.0  0.0   1.0  0.0  4.0  1.0  0.0  2.0  0.0  1.0                 11d    4.000                                                                              0.0  0.0   6.0  0.0  4.0  3.0  4.0  8.0  6.0  7.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0  0.0  0.0  2.0                 11e    4.000                                                                              0.0  0.0   0.0  0.0  3.0  7.0  7.0  3.0  1.0  2.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  0.0  0.0  0.0  0.0  1.0                 11f    4.000                                                                              0.0  0.0   6.0  0.0  9.0  9.0  6.0  5.0  9.0  7.0                         .500                                                                              0.0  0.0   0.0  0.0  2.0  3.0  0.0  0.0  0.0  3.0                 11g    4.000                                                                              3.0  1.0   6.0  1.0  9.0  5.0  5.0  6.0  7.0  7.0                         .500                                                                              0.0  0.0   0.0  0.0  3.0  2.0  3.0  2.0  2.0  5.0                 11h    4.000                                                                              0.0  0.0   0.0  0.0  0.0  3.0  2.0  7.0  3.0  0.0                 11i    4.000                                                                              0.0  0.0   7.0  0.0  4.0  9.0  7.0  9.0  6.0  7.0                         .500                                                                              0.0  0.0   0.0  0.0  0.0  4.0  4.0  0.0  0.0  2.0                 18a    4.000                                                                              5.0  8.0   9.0  7.0  9.0  9.0  7.0  9.0  9.0  9.0                        2.000                                                                              4.0  5.0   9.0  4.0  9.0  9.0  8.0  9.0  9.0  9.0                        1.000                                                                              0.0  0.0   8.0  3.0  7.0  6.0  6.0  9.0  7.0  7.0                         .500                                                                              0.0  0.0   6.0  0.0  2.0  7.0  5.0  9.0  6.0  7.0                 19a    4.000                                                                              5.0  4.0   9.0  4.0  9.0  9.0  9.0  9.0  9.0  9.0                        2.000                                                                              1.0  1.0   9.0  1.0  3.0  9.0  9.0  9.0  7.0  9.0                        1.000                                                                              0.0  0.0   9.0  2.0  4.0  9.0  9.0  9.0  8.0  9.0                         .500                                                                              0.0  0.0   9.0  0.0  2.0  9.0  9.0  9.0  6.0  9.0                 20a    4.000                                                                              3.0  4.0   9.0  3.0  9.0  9.0  7.0  9.0  9.0  9.0                        2.000                                                                              2.0  6.0   9.0  1.0  9.0  9.0  7.0  9.0  6.0  9.0                        1.000                                                                              1.0  3.0   9.0  1.0  9.0  9.0  7.0  9.0  7.0  8.0                         .500                                                                              1.0  1.0   8.0  0.0  3.0  9.0  6.0  7.0  6.0  8.0                 21a    4.000                                                                              5.0  5.0   9.0  4.0  9.0  9.0  8.0  9.0  9.0  9.0                        2.000                                                                              4.0  7.0   9.0  4.0  9.0  9.0  7.0  9.0  7.0  9.0                        1.000                                                                              4.0  4.0   9.0  4.0  9.0  9.0  7.0  9.0  8.0  9.0                         .500                                                                              0.0  3.0   9.0  3.0  3.0  9.0  6.0  7.0  5.0  9.0                 21b    4.000                                                                              4.0  2.0   9.0  7.0  9.0  9.0  9.0  9.0  9.0  9.0                        2.000                                                                              6.0  8.0   9.0  7.0  9.0  9.0  9.0  9.0  9.0  9.0                        1.000                                                                              3.0  2.0   9.0  5.0  9.0  7.0  9.0  9.0  9.0  8.0                         .500                                                                              5.0  3.0   9.0  5.0  9.0  8.0  8.0  9.0  9.0  8.0                 21c    4.000                                                                              0.0  0.0   9.0  1.0  5.0  9.0  8.0  7.0  4.0  5.0                        2.000                                                                              0.0  0.0   4.0  0.0  0.0  7.0  8.0  7.0  6.0  6.0                        1.000                                                                              0.0  0.0   4.0  0.0  0.0  9.0  7.0  6.0  3.0  6.0                         .500                                                                              0.0  0.0   4.0  0.0  0.0  3.0  6.0  5.0  1.0  3.0                 __________________________________________________________________________

What is claimed is:
 1. Intermediates having the structures: ##STR52##wherein A is hydrogen or methylR₁ is methyl; R₂ is isopropyl; W isoxygen or sulfur; and Q is ##STR53##
 2. A compound according to claim 1,4-isopropyl-2,4 -dimethyl-2-oxazolin-5-one.
 3. A compound according toclaim 1, 5-isopropyl-5-methyl-3-(p-tolylsulfonyl)hydantoin.